1H-pyrrolopyridine compound, N-oxide thereof or salt thereof, agricultural and horticultural insecticide comprising the compound, and method for using the insecticide

ABSTRACT

In crop production in the fields of agriculture, horticulture and the like, the damage caused by insect pests etc. is still immense, and insect pests resistant to existing insecticides have emerged. Under such circumstances, the development of novel agricultural and horticultural insecticides is desired. The present invention provides an agricultural and horticultural insecticide comprising a 1H-pyrrolo-condensed heterocyclic compound represented by the general formula (1): 
                         
{wherein A and A 1  each represent a nitrogen atom, R 3  and R 4  each represent a haloalkyl group, R 2  represents a hydrogen atom or an acetyl group, R 1  represents a halogen atom, and m represents 0 or 2}, an N-oxide thereof or a salt thereof as an active ingredient, and a method for using the insecticide.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a U.S. National Phase Application of PCTInternational Application Number PCT/JP2017/037089, filed on Oct. 12,2017, designating the United States of America and published in theJapanese language, which is an International Application of and claimsthe benefit of priority to Japanese Patent Application No. 2016-201628,filed on Oct. 13, 2016. The disclosures of the above-referencedapplications are hereby expressly incorporated by reference in theirentireties.

TECHNICAL FIELD

The present invention relates to a condensed heterocyclic compound or asalt thereof. More particularly, the present invention relates to anagricultural and horticultural insecticide comprising a1H-pyrrolo-condensed heterocyclic compound, such as certain kinds of1H-pyrrolopyridine compounds, an N-oxide thereof or a salt thereof as anactive ingredient, and a method for using the insecticide.

BACKGROUND ART

Various compounds have been examined for their potential as agriculturaland horticultural insecticides, and among them, certain kinds ofcondensed heterocyclic compounds have been reported to be useful asinsecticides (for example, see Patent Literature 1 to 7). Theliterature, however, does not disclose any 1H-pyrrolo-condensedheterocyclic compound.

CITATION LIST Patent Literature

Patent Literature 1: JP-A 2009-280574

Patent Literature 2: JP-A 2010-275301

Patent Literature 3: JP-A 2011-79774

Patent Literature 4: JP-A 2012-131780

Patent Literature 5: WO 2012/086848

Patent Literature 6: WO 2013/018928

Patent literature 7: WO 2014/157600

SUMMARY OF INVENTION Technical Problem

In crop production in the fields of agriculture, horticulture and thelike, the damage caused by insect pests etc. is still immense, and theemergence of insect pests resistant to existing insecticides is agrowing problem. In addition, environmental protection on the earth is aglobal challenge to be addressed in every field, including theagricultural and horticultural field. Therefore, the development ofnovel compounds as agricultural and horticultural insecticides havinglow environmental burden is desired.

Solution to Problem

The present inventors conducted extensive research to solve theabove-described problems. As a result, the present inventors found thata 1H-pyrrolo-condensed heterocyclic compound represented by the generalformula (1), an N-oxide thereof and a salt thereof are highly effectivefor the control of agricultural and horticultural pests and have lowenvironmental burden. Based on this finding, the present inventorscompleted the present invention.

That is, the present invention includes the following.

[1] A condensed heterocyclic compound represented by the general formula(1):

{wherein

R¹ represents

(a1) a halogen atom;

(a2) a cyano group;

(a3) a (C₁-C₆) alkyl group;

(a4) a (C₃-C₆) cycloalkyl group;

(a5) a (C₂-C₆) alkenyl group;

(a6) a (C₂-C₆) alkynyl group;

(a7) a (C₁-C₆) alkylcarbonyl group; or

(a8) a (C₁-C₆) alkoxycarbonyl group,

R² represents

(b1) a hydrogen atom;

(b2) a (C₁-C₆) alkyl group;

(b3) a (C₁-C₆) alkylcarbonyl group;

(b4) a (C₁-C₆) alkoxycarbonyl group;

(b5) a halo (C₁-C₆) alkoxy group;

(b6) a (C₁-C₆) alkoxy (C₁-C₆) alkyl group;

(b7) a (C₁-C₆) alkylthio (C₁-C₆) alkyl group;

(b8) a (C₂-C₆) alkenyl group;

(b9) a (C₂-C₆) alkynyl group; or

(b10) a (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group,

R³ represents

(c1) a hydrogen atom;

(c2) a halogen atom;

(c3) a cyano group;

(c4) a nitro group;

(c5) a (C₁-C₆) alkyl group;

(c6) a (C₃-C₆) cycloalkyl group;

(c7) a cyano (C₃-C₆) cycloalkyl group;

(c8) a (C₁-C₆) alkoxy group;

(c9) a halo (C₁-C₆) alkyl group;

(c10) a halo (C₁-C₆) alkoxy group;

(c11) a (C₁-C₆) alkylthio group;

(c12) a halo (C₁-C₆) alkylthio group;

(c13) a (C₁-C₆) alkylsulfinyl group;

(c14) a halo (C₁-C₆) alkylsulfinyl group;

(c15) a (C₁-C₆) alkylsulfonyl group; or

(c16) a halo (C₁-C₆) alkylsulfonyl group,

R⁴ and R⁵ may be the same or different, and each represent

(d1) a hydrogen atom;

(d2) a halogen atom;

(d3) a cyano group;

(d4) a nitro group;

(d4) a formyl group;

(d5) a (C₁-C₆) alkyl group;

(d6) a (C₁-C₆) alkoxy group;

(d7) a (C₃-C₆) cycloalkyl group;

(d8) an R⁶(R⁷)N group (wherein R⁶ and R⁷ may be the same or different,and each represent a hydrogen atom, a (C₁-C₆) alkyl group, a (C₃-C₆)cycloalkyl group, a (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group, a halo(C₁-C₆) alkyl group, a (C₁-C₆) alkylcarbonyl group, a (C₁-C₆)alkoxycarbonyl group, a phenyl group or a phenyl (C₁-C₆) alkyl group);(d9) a C(R⁶)═NOR⁷ group (wherein R⁶ and R⁷ are as defined above);(d10) a halo (C₁-C₆) alkyl group;(d11) a halo (C₁-C₆) alkoxy group;(d12) a (C₁-C₆) alkylthio group;(d13) a halo (C₁-C₆) alkylthio group;(d14) a (C₁-C₆) alkylsulfinyl group;(d15) a halo (C₁-C₆) alkylsulfinyl group;(d16) a (C₁-C₆) alkylsulfonyl group;(d17) a halo (C₁-C₆) alkylsulfonyl group;(d18) a (C₁-C₆) alkylcarbonyl group;(d19) an aryl group;(d20) an aryl group having, on the ring, 1 to 5 substituting groupswhich may be the same or different and are selected from (a) a halogenatom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a(C₁-C₆) alkyl group, (f) a halo (C₁-C₆) alkyl group, (g) a (C₁-C₆)alkoxy group, (h) a halo (C₁-C₆) alkoxy group, (i) a (C₃-C₆) cycloalkyl(C₁-C₆) alkoxy group, (j) a (C₁-C₆) alkylthio group, (k) a halo (C₁-C₆)alkylthio group, (l) a (C₁-C₆) alkylsulfinyl group, (m) a halo (C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆) alkylsulfonyl group, (o) a halo(C₁-C₆) alkylsulfonyl group, (p) a (C₁-C₆) alkylcarbonyl group, (q) acarboxyl group and (r) a (C₁-C₆) alkoxycarbonyl group;(d21) a heterocyclic group;(d22) a heterocyclic group having, on the ring, 1 or 2 substitutinggroups which may be the same or different and are selected from (a) ahalogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group,(e) a (C₁-C₆) alkyl group, (f) a halo (C₁-C₆) alkyl group, (g) a (C₁-C₆)alkoxy group, (h) a halo (C₁-C₆) alkoxy group, (i) a (C₃-C₆) cycloalkyl(C₁-C₆) alkoxy group, (j) a (C₁-C₆) alkylthio group, (k) a halo (C₁-C₆)alkylthio group, (l) a (C₁-C₆) alkylsulfinyl group, (m) a halo (C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆) alkylsulfonyl group, (o) a halo(C₁-C₆) alkylsulfonyl group, (p) a (C₁-C₆) alkylcarbonyl group, (q) acarboxyl group and (r) a (C₁-C₆) alkoxycarbonyl group;(d23) an aryloxy group;(d24) an aryloxy group having, on the ring, 1 to 5 substituting groupswhich may be the same or different and are selected from (a) a halogenatom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a(C₁-C₆) alkyl group, (f) a halo (C₁-C₆) alkyl group, (g) a (C₁-C₆)alkoxy group, (h) a halo (C₁-C₆) alkoxy group, (i) a (C₃-C₆) cycloalkyl(C₁-C₆) alkoxy group, (j) a (C₁-C₆) alkylthio group, (k) a halo (C₁-C₆)alkylthio group, (l) a (C₁-C₆) alkylsulfinyl group, (m) a halo (C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆) alkylsulfonyl group, (o) a halo(C₁-C₆) alkylsulfonyl group, (p) a (C₁-C₆) alkylcarbonyl group, (q) acarboxyl group and (r) a (C₁-C₆) alkoxycarbonyl group;(d25) an aryl (C₁-C₆) alkoxy group; or(d26) an aryl (C₁-C₆) alkoxy group having, on the ring, 1 to 5substituting groups which may be the same or different and are selectedfrom (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) aformyl group, (e) a (C₁-C₆) alkyl group, (f) a halo (C₁-C₆) alkyl group,(g) a (C₁-C₆) alkoxy group, (h) a halo (C₁-C₆) alkoxy group, (i) a(C₃-C₆) cycloalkyl (C₁-C₆) alkoxy group, (j) a (C₁-C₆) alkylthio group,(k) a halo (C₁-C₆) alkylthio group, (l) a (C₁-C₆) alkylsulfinyl group,(m) a halo (C₁-C₆) alkylsulfinyl group, (n) a (C₁-C₆) alkylsulfonylgroup, (o) a halo (C₁-C₆) alkylsulfonyl group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group and (r) a (C₁-C₆)alkoxycarbonyl group,

A and A¹ may be the same or different, and each represent a nitrogenatom, an N-oxide or a C—R⁸ group (wherein R⁸ represents (e1) a hydrogenatom; (e2) a halogen atom; (e3) a cyano group; (e4) a nitro group; (e5)a formyl group; (e6) a (C₁-C₆) alkyl group; or (e7) a (C₁-C₆) alkoxygroup), and

m represents 0, 1 or 2}, an N-oxide thereof or a salt thereof.

[2] The condensed heterocyclic compound, the N-oxide or the saltaccording to the above [1], wherein

R¹ represents

(a1) a halogen atom;

(a2) a cyano group;

(a3) a (C₁-C₆) alkyl group;

(a5) a (C₂-C₆) alkenyl group; or

(a8) a (C₁-C₆) alkoxycarbonyl group,

R² represents

(b1) a hydrogen atom;

(b2) a (C₁-C₆) alkyl group;

(b3) a (C₁-C₆) alkylcarbonyl group;

(b4) a (C₁-C₆) alkoxycarbonyl group;

(b5) a halo (C₁-C₆) alkoxy group;

(b6) a (C₁-C₆) alkoxy (C₁-C₆) alkyl group;

(b7) a (C₁-C₆) alkylthio (C₁-C₆) alkyl group;

(b8) a (C₂-C₆) alkenyl group;

(b9) a (C₂-C₆) alkynyl group; or

(b10) a (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group,

R³ represents (c9) a halo (C₁-C₆) alkyl group, R⁴ and R⁵ may be the sameor different, and each represent

(d2) a halogen atom;

(d4) a formyl group;

(d6) a (C₁-C₆) alkoxy group;

(d7) a (C₃-C₆) cycloalkyl group;

(d8) an R⁶(R⁷)N group (wherein R⁶ and R⁷ may be the same or different,and each represent a hydrogen atom, a (C₁-C₆) alkyl group, a (C₃-C₆)cycloalkyl group, a (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group, a halo(C₁-C₆) alkyl group, a (C₁-C₆) alkylcarbonyl group, a (C₁-C₆)alkoxycarbonyl group, a phenyl group or a phenyl (C₁-C₆) alkyl group);(d9) a C(R⁶)═NOR⁷ group (wherein R⁶ and R⁷ are as defined above);(d10) a halo (C₁-C₆) alkyl group;(d11) a halo (C₁-C₆) alkoxy group;(d12) a (C₁-C₆) alkylthio group;(d13) a halo (C₁-C₆) alkylthio group;(d16) a (C₁-C₆) alkylsulfonyl group;(d18) a (C₁-C₆) alkylcarbonyl group;(d20) an aryl group having, on the ring, 1 to 5 substituting groupswhich may be the same or different and are selected from (a) a halogenatom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a(C₁-C₆) alkyl group, (f) a halo (C₁-C₆) alkyl group, (g) a (C₁-C₆)alkoxy group, (h) a halo (C₁-C₆) alkoxy group, (i) a (C₃-C₆) cycloalkyl(C₁-C₆) alkoxy group, (j) a (C₁-C₆) alkylthio group, (k) a halo (C₁-C₆)alkylthio group, (l) a (C₁-C₆) alkylsulfinyl group, (m) a halo (C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆) alkylsulfonyl group, (o) a halo(C₁-C₆) alkylsulfonyl group, (p) a (C₁-C₆) alkylcarbonyl group, (q) acarboxyl group and (r) a (C₁-C₆) alkoxycarbonyl group;(d21) a heterocyclic group;(d22) a heterocyclic group having, on the ring, 1 or 2 substitutinggroups which may be the same or different and are selected from (a) ahalogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group,(e) a (C₁-C₆) alkyl group, (f) a halo (C₁-C₆) alkyl group, (g) a (C₁-C₆)alkoxy group, (h) a halo (C₁-C₆) alkoxy group, (i) a (C₃-C₆) cycloalkyl(C₁-C₆) alkoxy group, (j) a (C₁-C₆) alkylthio group, (k) a halo (C₁-C₆)alkylthio group, (l) a (C₁-C₆) alkylsulfinyl group, (m) a halo (C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆) alkylsulfonyl group, (o) a halo(C₁-C₆) alkylsulfonyl group, (p) a (C₁-C₆) alkylcarbonyl group, (q) acarboxyl group and (r) a (C₁-C₆) alkoxycarbonyl group;(d24) an aryloxy group having, on the ring, 1 to 5 substituting groupswhich may be the same or different and are selected from (a) a halogenatom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a(C₁-C₆) alkyl group, (f) a halo (C₁-C₆) alkyl group, (g) a (C₁-C₆)alkoxy group, (h) a halo (C₁-C₆) alkoxy group, (i) a (C₃-C₆) cycloalkyl(C₁-C₆) alkoxy group, (j) a (C₁-C₆) alkylthio group, (k) a halo (C₁-C₆)alkylthio group, (l) a (C₁-C₆) alkylsulfinyl group, (m) a halo (C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆) alkylsulfonyl group, (o) a halo(C₁-C₆) alkylsulfonyl group, (p) a (C₁-C₆) alkylcarbonyl group, (q) acarboxyl group and (r) a (C₁-C₆) alkoxycarbonyl group;(d25) an aryl (C₁-C₆) alkoxy group; or(d26) an aryl (C₁-C₆) alkoxy group having, on the ring, 1 to 5substituting groups which may be the same or different and are selectedfrom (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) aformyl group, (e) a (C₁-C₆) alkyl group, (f) a halo (C₁-C₆) alkyl group,(g) a (C₁-C₆) alkoxy group, (h) a halo (C₁-C₆) alkoxy group, (i) a(C₃-C₆) cycloalkyl (C₁-C₆) alkoxy group, (j) a (C₁-C₆) alkylthio group,(k) a halo (C₁-C₆) alkylthio group, (l) a (C₁-C₆) alkylsulfinyl group,(m) a halo (C₁-C₆) alkylsulfinyl group, (n) a (C₁-C₆) alkylsulfonylgroup, (o) a halo (C₁-C₆) alkylsulfonyl group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group and (r) a (C₁-C₆)alkoxycarbonyl group.[3] The condensed heterocyclic compound, the N-oxide or the saltaccording to the above [1], wherein

R¹ represents

(a1) a halogen atom;

(a2) a cyano group;

(a3) a (C₁-C₆) alkyl group;

(a5) a (C₂-C₆) alkenyl group; or

(a8) a (C₁-C₆) alkoxycarbonyl group,

R² represents

(b1) a hydrogen atom;

(b2) a (C₁-C₆) alkyl group;

(b3) a (C₁-C₆) alkylcarbonyl group;

(b4) a (C₁-C₆) alkoxycarbonyl group;

(b5) a halo (C₁-C₆) alkoxy group;

(b6) a (C₁-C₆) alkoxy (C₁-C₆) alkyl group;

(b7) a (C₁-C₆) alkylthio (C₁-C₆) alkyl group;

(b8) a (C₂-C₆) alkenyl group;

(b9) a (C₂-C₆) alkynyl group; or

(b10) a (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group,

R³ represents (c9) a halo (C₁-C₆) alkyl group,

R⁴ and R⁵ may be the same or different, and each represent

(d2) a halogen atom;

(d4) a formyl group;

(d6) a (C₁-C₆) alkoxy group;

(d7) a (C₃-C₆) cycloalkyl group;

(d9) a C(R⁶)═NOR⁷ group (wherein R⁶ and R⁷ may be the same or different,and each represent a hydrogen atom, a (C₁-C₆) alkyl group, a (C₃-C₆)cycloalkyl group, a (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group, a halo(C₁-C₆) alkyl group, a (C₁-C₆) alkylcarbonyl group, a (C₁-C₆)alkoxycarbonyl group, a phenyl group or a phenyl (C₁-C₆) alkyl group);(d10) a halo (C₁-C₆) alkyl group;(d11) a halo (C₁-C₆) alkoxy group;(d20) an aryl group having, on the ring, 1 to 5 substituting groupswhich may be the same or different and are selected from (a) a halogenatom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a(C₁-C₆) alkyl group, (f) a halo (C₁-C₆) alkyl group, (g) a (C₁-C₆)alkoxy group, (h) a halo (C₁-C₆) alkoxy group, (i) a (C₃-C₆) cycloalkyl(C₁-C₆) alkoxy group, (j) a (C₁-C₆) alkylthio group, (k) a halo (C₁-C₆)alkylthio group, (l) a (C₁-C₆) alkylsulfinyl group, (m) a halo (C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆) alkylsulfonyl group, (o) a halo(C₁-C₆) alkylsulfonyl group, (p) a (C₁-C₆) alkylcarbonyl group, (q) acarboxyl group and (r) a (C₁-C₆) alkoxycarbonyl group;(d21) a heterocyclic group;(d22) a heterocyclic group having, on the ring, 1 or 2 substitutinggroups which may be the same or different and are selected from (a) ahalogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group,(e) a (C₁-C₆) alkyl group, (f) a halo (C₁-C₆) alkyl group, (g) a (C₁-C₆)alkoxy group, (h) a halo (C₁-C₆) alkoxy group, (i) a (C₃-C₆) cycloalkyl(C₁-C₆) alkoxy group, (j) a (C₁-C₆) alkylthio group, (k) a halo (C₁-C₆)alkylthio group, (l) a (C₁-C₆) alkylsulfinyl group, (m) a halo (C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆) alkylsulfonyl group, (o) a halo(C₁-C₆) alkylsulfonyl group, (p) a (C₁-C₆) alkylcarbonyl group, (q) acarboxyl group and (r) a (C₁-C₆) alkoxycarbonyl group;(d24) an aryloxy group having, on the ring, 1 to 5 substituting groupswhich may be the same or different and are selected from (a) a halogenatom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a(C₁-C₆) alkyl group, (f) a halo (C₁-C₆) alkyl group, (g) a (C₁-C₆)alkoxy group, (h) a halo (C₁-C₆) alkoxy group, (i) a (C₃-C₆) cycloalkyl(C₁-C₆) alkoxy group, (j) a (C₁-C₆) alkylthio group, (k) a halo (C₁-C₆)alkylthio group, (l) a (C₁-C₆) alkylsulfinyl group, (m) a halo (C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆) alkylsulfonyl group, (o) a halo(C₁-C₆) alkylsulfonyl group, (p) a (C₁-C₆) alkylcarbonyl group, (q) acarboxyl group and (r) a (C₁-C₆) alkoxycarbonyl group;(d25) an aryl (C₁-C₆) alkoxy group; or(d26) an aryl (C₁-C₆) alkoxy group having, on the ring, 1 to 5substituting groups which may be the same or different and are selectedfrom (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) aformyl group, (e) a (C₁-C₆) alkyl group, (f) a halo (C₁-C₆) alkyl group,(g) a (C₁-C₆) alkoxy group, (h) a halo (C₁-C₆) alkoxy group, (i) a(C₃-C₆) cycloalkyl (C₁-C₆) alkoxy group, (j) a (C₁-C₆) alkylthio group,(k) a halo (C₁-C₆) alkylthio group, (l) a (C₁-C₆) alkylsulfinyl group,(m) a halo (C₁-C₆) alkylsulfinyl group, (n) a (C₁-C₆) alkylsulfonylgroup, (o) a halo (C₁-C₆) alkylsulfonyl group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group and (r) a (C₁-C₆)alkoxycarbonyl group.[4] Use of the condensed heterocyclic compound, the N-oxide or the saltaccording to any of the above [1] to [3] as an agricultural andhorticultural insecticide.[5] A method for using an agricultural and horticultural insecticide,comprising treating plants or soil with an active ingredient of theagricultural and horticultural insecticide specified in the above [4].[6] A method for controlling agricultural and horticultural pests,comprising treating plants or soil with an effective amount of theagricultural and horticultural insecticide specified in the above [4].[7] An animal ectoparasite control agent comprising the condensedheterocyclic compound, the N-oxide or the salt according to any of theabove [1] to [3] as an active ingredient.[8] A method for controlling animal ectoparasites, comprising treatinganimal ectoparasites with an effective amount of the animal ectoparasitecontrol agent according to the above [7].

Advantageous Effects of Invention

The 1H-pyrrolo-condensed heterocyclic compound of the present invention,an N-oxide thereof and a salt thereof are not only highly effective asan agricultural and horticultural insecticide but also effective againstpests which live on pets such as dogs and cats and domestic animals suchas cattle and sheep.

DESCRIPTION OF EMBODIMENTS

In the definitions of the general formula (1) representing the1H-pyrrolo-condensed heterocyclic compound of the present invention, anN-oxide thereof or a salt thereof, “halo” refers to a “halogen atom” andrepresents a chlorine atom, a bromine atom, an iodine atom or a fluorineatom.

The “(C₁-C₆) alkyl group” refers to a straight-chain or branched-chainalkyl group of 1 to 6 carbon atoms, for example, a methyl group, anethyl group, a n-propyl group, an isopropyl group, a n-butyl group, anisobutyl group, a sec-butyl group, a tert-butyl group, a n-pentyl group,an isopentyl group, a tert-pentyl group, a neopentyl group, a2,3-dimethylpropyl group, an 1-ethylpropyl group, a 1-methylbutyl group,a 2-methylbutyl group, a n-hexyl group, an isohexyl group, a 2-hexylgroup, a 3-hexyl group, a 2-methylpentyl group, a 3-methylpentyl group,a 1,1,2-trimethyl propyl group, a 3,3-dimethylbutyl group or the like.The “(C₂-C₆) alkenyl group” refers to a straight-chain or branched-chainalkenyl group of 2 to 6 carbon atoms, for example, a vinyl group, anallyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group,a 2-methyl-2-propenyl group, a 1-methyl-2-propenyl group, a2-methyl-1-propenyl group, a pentenyl group, a 1-hexenyl group, a3,3-dimethyl-1-butenyl group or the like. The “(C₂-C₆) alkynyl group”refers to a straight-chain or branched-chain alkynyl group of 2 to 6carbon atoms, for example, an ethynyl group, a 1-propynyl group, a2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynylgroup, a 3-methyl-1-propynyl group, a 2-methyl-3-propynyl group, apentynyl group, a 1-hexynyl group, a 3-methyl-1-butynyl group, a3,3-dimethyl-1-butynyl group or the like.

The “(C₃-C₆) cycloalkyl group” refers to a cyclic alkyl group of 3 to 6carbon atoms, for example, a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a cyclohexyl group or the like. The “(C₁-C₆) alkoxygroup” refers to a straight-chain or branched-chain alkoxy group of 1 to6 carbon atoms, for example, a methoxy group, an ethoxy group, an-propoxy group, an isopropoxy group, a n-butoxy group, a sec-butoxygroup, a tert-butoxy group, a n-pentyloxy group, an isopentyloxy group,a tert-pentyloxy group, a neopentyloxy group, a 2,3-dimethylpropyloxygroup, an 1-ethylpropyloxy group, a 1-methylbutyloxy group, a n-hexyloxygroup, an isohexyloxy group, a 1,1,2-trimethylpropyloxy group or thelike. The “(C₂-C₆) alkenyloxy group” refers to a straight-chain orbranched-chain alkenyloxy group of 2 to 6 carbon atoms, for example, apropenyloxy group, a butenyloxy group, a pentenyloxy group, a hexenyloxygroup or the like. The “(C₂-C₆) alkynyloxy group” refers to astraight-chain or branched-chain alkynyloxy group of 2 to 6 carbonatoms, for example, a propynyloxy group, a butynyloxy group, apentynyloxy group, a hexynyloxy group or the like.

The “(C₁-C₆) alkylthio group” refers to a straight-chain orbranched-chain alkylthio group of 1 to 6 carbon atoms, for example, amethylthio group, an ethylthio group, a n-propylthio group, anisopropylthio group, a n-butylthio group, a sec-butylthio group, atert-butylthio group, a n-pentylthio group, an isopentylthio group, atert-pentylthio group, a neopentylthio group, a 2,3-dimethylpropylthiogroup, an 1-ethylpropylthio group, a 1-methylbutylthio group, an-hexylthio group, an isohexylthio group, a 1,1,2-trimethylpropylthiogroup or the like. The “(C₁-C₆) alkylsulfinyl group” refers to astraight-chain or branched-chain alkylsulfinyl group of 1 to 6 carbonatoms, for example, a methylsulfinyl group, an ethylsulfinyl group, an-propylsulfinyl group, an isopropylsulfinyl group, a n-butylsulfinylgroup, a sec-butylsulfinyl group, a tert-butylsulfinyl group, an-pentylsulfinyl group, an isopentylsulfinyl group, atert-pentylsulfinyl group, a neopentylsulfinyl group, a2,3-dimethylpropylsulfinyl group, an 1-ethylpropylsulfinyl group, a1-methylbutylsulfinyl group, a n-hexylsulfinyl group, anisohexylsulfinyl group, a 1,1,2-trimethylpropylsulfinyl group or thelike. The “(C₁-C₆) alkylsulfonyl group” refers to a straight-chain orbranched-chain alkylsulfonyl group of 1 to 6 carbon atoms, for example,a methylsulfonyl group, an ethylsulfonyl group, a n-propylsulfonylgroup, an isopropylsulfonyl group, a n-butylsulfonyl group, asec-butylsulfonyl group, a tert-butylsulfonyl group, a n-pentylsulfonylgroup, an isopentylsulfonyl group, a tert-pentylsulfonyl group, aneopentylsulfonyl group, a 2,3-dimethylpropylsulfonyl group, an1-ethylpropylsulfonyl group, a 1-methylbutylsulfonyl group, an-hexylsulfonyl group, an isohexylsulfonyl group, a1,1,2-trimethylpropylsulfonyl group or the like.

The “(C₂-C₆) alkenylthio group” refers to a straight-chain orbranched-chain alkenylthio group of 2 to 6 carbon atoms, for example, apropenylthio group, a butenylthio group, a pentenylthio group, ahexenylthio group or the like. The “(C₂-C₆) alkynylthio group” refers toa straight-chain or branched-chain alkynylthio group of 2 to 6 carbonatoms, for example, a propynylthio group, a butynylthio group, apentynylthio group, a hexynylthio group or the like.

The “(C₂-C₆) alkenylsulfinyl group” refers to a straight-chain orbranched-chain alkenylsulfinyl group of 2 to 6 carbon atoms, forexample, a propenylsulfinyl group, a butenylsulfinyl group, apentenylsulfinyl group, a hexenylsulfinyl group or the like. The“(C₂-C₆) alkynylsulfinyl group” refers to a straight-chain orbranched-chain alkynylsulfinyl group of 2 to 6 carbon atoms, forexample, a propynylsulfinyl group, a butynylsulfinyl group, apentynylsulfinyl group, a hexynylsulfinyl group or the like.

The “(C₂-C₆) alkenylsulfonyl group” refers to a straight-chain orbranched-chain alkenylsulfonyl group of 2 to 6 carbon atoms, forexample, a propenylsulfonyl group, a butenylsulfonyl group, apentenylsulfonyl group, a hexenylsulfonyl group or the like. The“(C₂-C₆) alkynylsulfonyl group” refers to a straight-chain orbranched-chain alkynylsulfonyl group of 2 to 6 carbon atoms, forexample, a propynylsulfonyl group, a butynylsulfonyl group, apentynylsulfonyl group, a hexynylsulfonyl group or the like.

The “(C₁-C₆) alkylcarbonyl group” refers to a straight-chain orbranched-chain alkylcarbonyl group of 1 to 6 carbon atoms, for example,a methylcarbonyl group, an ethylcarbonyl group, a n-propylcarbonylgroup, an isopropylcarbonyl group, a n-butylcarbonyl group, asec-butylcarbonyl group, a tert-butylcarbonyl group, a n-pentylcarbonylgroup, an isopentylcarbonyl group, a tert-pentylcarbonyl group, aneopentylcarbonyl group, a 2,3-dimethylpropylcarbonyl group, an1-ethylpropylcarbonyl group, a 1-methylbutylcarbonyl group, an-hexylcarbonyl group, an isohexylcarbonyl group, a1,1,2-trimethylpropylcarbonyl group or the like. The “(C₁-C₆)alkoxycarbonyl group” refers to a straight-chain or branched-chainalkoxycarbonyl group of 1 to 6 carbon atoms, for example, amethoxycarbonyl group, an ethoxycarbonyl group, a n-propoxycarbonylgroup, an isopropoxycarbonyl group, a n-butoxycarbonyl group, asec-butoxycarbonyl group, a tert-butoxycarbonyl group, an-pentoxycarbonyl group, an isopentyloxycarbonyl group, atert-pentyloxycarbonyl group, a neopentyloxycarbonyl group, a2,3-dimethylpropyloxycarbonyl group, an 1-ethylpropyloxycarbonyl group,a 1-methylbutyloxycarbonyl group, a n-hexyloxycarbonyl group, anisohexyloxycarbonyl group, a 1,1,2-trimethylpropyloxycarbonyl group orthe like.

The “(C₃-C₆) cycloalkoxy group” refers to a cyclic alkoxy group of 3 to6 carbon atoms, for example, a cyclopropoxy group, a cyclobutoxy group,a cyclopentyloxy group, a cyclohexyloxy group or the like. The “(C₃-C₆)cycloalkylthio group” refers to a cyclic alkylthio group of 3 to 6carbon atoms, for example, a cyclopropylthio group, a cyclobutylthiogroup, a cyclopentylthio group, a cyclohexylthio group or the like. The“(C₃-C₆) cycloalkylsulfinyl group” refers to a cyclic alkylsulfinylgroup of 3 to 6 carbon atoms, for example, a cyclopropylsulfinyl group,a cyclobutylsulfinyl group, a cyclopentylsulfinyl group, acyclohexylsulfinyl group or the like. The “(C₃-C₆) cycloalkylsulfonylgroup” refers to a cyclic alkylsulfonyl group of 3 to 6 carbon atoms,for example, a cyclopropylsulfonyl group, a cyclobutylsulfonyl group, acyclopentylsulfonyl group, a cyclohexylsulfonyl group or the like.

The above-mentioned “(C₁-C₆) alkyl group”, “(C₂-C₆) alkenyl group”,“(C₂-C₆) alkynyl group”, “(C₁-C₆) alkylcarbonyl group”, “(C₁-C₆)alkoxycarbonyl group”, “(C₃-C₆) cycloalkyl group”, “(C₃-C₆)cycloalkyloxy group”, “(C₁-C₆) alkoxy group”, “(C₂-C₆) alkenyloxygroup”, “(C₂-C₆) alkynyloxy group”, “(C₁-C₆) alkylthio group”, “(C₁-C₆)alkylsulfinyl group”, “(C₁-C₆) alkylsulfonyl group”, “(C₂-C₆)alkenylthio group”, “(C₂-C₆) alkynylthio group”, “(C₂-C₆)alkenylsulfinyl group”, “(C₂-C₆) alkynylsulfinyl group”, “(C₂-C₆)alkenylsulfonyl group”, “(C₂-C₆) alkynylsulfonyl group”, “(C₃-C₆)cycloalkylthio group”, “(C₃-C₆) cycloalkylsulfinyl group” and “(C₃-C₆)cycloalkylsulfonyl group” may be substituted with one or more halogenatoms at a substitutable position(s), and in the case where any of theabove-listed groups is substituted with two or more halogen atoms, thehalogen atoms may be the same or different.

The above-mentioned “groups substituted with one or more halogen atoms”are expressed as a “halo (C₁-C₆) alkyl group”, a “halo (C₂-C₆) alkenylgroup”, a “halo (C₂-C₆) alkynyl group”, “a halo (C₁-C₆) alkylcarbonylgroup”, “a halo (C₁-C₆) alkoxycarbonyl group”, a “halo (C₃-C₆)cycloalkyl group”, a “halo (C₃-C₆) cycloalkyloxy group”, a “halo (C₁-C₆)alkoxy group”, a “halo (C₂-C₆) alkenyloxy group”, a “halo (C₂-C₆)alkynyloxy group”, a “halo (C₁-C₆) alkylthio group”, a “halo (C₁-C₆)alkylsulfinyl group”, a “halo (C₁-C₆) alkylsulfonyl group”, a “halo(C₂-C₆) alkenylthio group”, a “halo (C₂-C₆) alkynylthio group”, a “halo(C₂-C₆) alkenylsulfinyl group”, a “halo (C₂-C₆) alkynylsulfinyl group”,a “halo (C₂-C₆) alkenylsulfonyl group”, a “halo (C₂-C₆) alkynylsulfonylgroup”, a “halo (C₃-C₆) cycloalkylthio group”, a “halo (C₃-C₆)cycloalkylsulfinyl group” and a “halo (C₃-C₆) cycloalkylsulfonyl group”.

The expressions “(C₁-C₆)”, “(C₂-C₆)”, “(C₃-C₆)”, etc. each refer to therange of the number of carbon atoms in each group. The same definitionholds true for groups in which two or more of the above-mentioned groupsare coupled together, and for example, the “(C₁-C₆) alkoxy (C₁-C₆) alkylgroup” means that a straight-chain or branched-chain alkoxy group of 1to 6 carbon atoms is bound to a straight-chain or branched-chain alkylgroup of 1 to 6 carbon atoms.

The “3- to 6-membered aliphatic ring group” which R⁴ and R⁵ bound to thesame carbon atom are joined together to form is exemplified by acyclopropyl group, a cyclobutyl group, a cyclopentyl group and acyclohexyl group. The “aromatic ring group or aromatic heterocyclic ringgroup” which R⁴ and R⁵ are combined to form is exemplified by a quinolylor naphthyl group having a phenyl ring formed of R⁴ and R⁵.

The “aryl group” refers to an aromatic hydrocarbon group of 6 to 10carbon atoms, for example, a phenyl group, a 1-naphthyl group, a2-naphthyl group or the like. The aryl group is particularly preferablya phenyl group. The “aryloxy group” refers to, for example, a phenoxygroup, a 1-naphthyloxy group, a 2-naphthyloxy group or the like.

The “heterocyclic group” and “heterocyclic ring” refer to a 5- or6-membered monocyclic aromatic or 4- to 6-membered monocyclicnon-aromatic heterocyclic group containing, as ring atoms, one or morecarbon atoms and 1 to 4 heteroatoms selected from an oxygen atom, asulfur atom and a nitrogen atom; and also refer to a condensed aromaticheterocyclic group formed by condensation of such a monocyclic aromaticheterocycle with a benzene ring or to a condensed aromatic heterocyclicgroup formed by condensation of such a monocyclic aromatic heterocyclewith a monocyclic aromatic ring, for example, a benzene ring.

Examples of the “aromatic heterocyclic group” include monocyclicaromatic heterocyclic groups such as a furyl group, a thienyl group, apyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinylgroup, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, athiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolylgroup, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, atetrazolyl group and a triazinyl group; and condensed aromaticheterocyclic groups such as a quinolyl group, an isoquinolyl group, aquinazolyl group, a quinoxalyl group, a benzofuranyl group, abenzothienyl group, a benzoxazolyl group, a benzisoxazolyl group, abenzothiazolyl group, a benzimidazolyl group, a benzotriazolyl group, anindolyl group, an indazolyl group, a pyrrolopyrazinyl group, animidazopyridinyl group, an imidazopyrazinyl group, a pyrazolopyridinylgroup, a pyrazolothienyl group and a pyrazolotriazinyl group.

Examples of the “non-aromatic heterocyclic group” include monocyclicnon-aromatic heterocyclic groups such as an oxetanyl group, a thietanylgroup, an azetidinyl group, a pyrrolidinyl group, a pyrrolidinyl-2-onegroup, a piperidinyl group, a morpholinyl group, a thiomorpholinylgroup, a piperazinyl group, a hexamethyleneiminyl group, an oxazolidinylgroup, a thiazolidinyl group, an imidazolidinyl group, an oxazolinylgroup, a thiazolinyl group, an isoxazolinyl group, an imidazolinylgroup, a dioxolyl group, a dioxolanyl group, a dihydrooxadiazolyl group,an 2-oxo-pyrrolidin-1-yl group, an 2-oxo-1,3-oxazolidin-5-yl group, an5-oxo-1,2,4-oxadiazolin-3-yl group, a 1,3-dioxolan-2-yl group, a1,3-dioxan-2-yl group, a 1,3-dioxepan-2-yl group, a pyranyl group, atetrahydropyranyl group, a thiopyranyl group, a tetrahydrothiopyranylgroup, an 1-oxide tetrahydrothiopyranyl group, a 1,1-dioxidetetrahydrothiopyranyl group, a tetrahydrofuranyl group, a dioxanylgroup, a pyrazolidinyl group, a pyrazolinyl group, atetrahydropyrimidinyl group, a dihydrotriazolyl group and atetrahydrotriazolyl group.

Preferable examples of the “heterocyclic group” include an isoxazolylgroup, a pyrimidinyl group, a pyrazinyl group, a pyridyl group, apyrazolyl group, a thiazoyl group, a thienyl group, a pyrrolyl group, abenzimidazolyl group, a benzofuranyl group, a benzothienyl group and apyrrolidinyl-2-one group.

Examples of the salt of the 1H-pyrrolo-condensed heterocyclic compoundrepresented by the general formula (1) of the present invention or anN-oxide thereof include inorganic acid salts, such as hydrochlorides,sulfates, nitrates and phosphates; organic acid salts, such as acetates,fumarates, maleates, oxalates, methanesulfonates, benzenesulfonates andp-toluenesulfonates; and salts with an inorganic or organic base such asa sodium ion, a potassium ion, a calcium ion and a trimethylammoniumion.

The 1H-pyrrolo-condensed heterocyclic compound represented by thegeneral formula (1) of the present invention, an N-oxide thereof and asalt thereof can have one or more chiral centers in the structuralformula, and can exist as two or more kinds of optical isomers ordiastereomers. All the optical isomers and mixtures of the isomers atany ratio are also included in the present invention. Further, thecompound represented by the general formula (1) of the presentinvention, an N-oxide thereof and a salt thereof can exist as two kindsof geometric isomers due to a carbon-carbon double bond or acarbon-nitrogen double bond in the structural formula. All the geometricisomers and mixtures of the isomers at any ratio are also included inthe present invention.

The 1H-pyrrolo-condensed heterocyclic compound of the present invention,an N-oxide thereof or a salt thereof can be produced according to acombination of known methods or methods known per se, for example, theproduction method described below, which is a non-limiting example.Another or other well-established reactions may also be used asrequired.

Production Method 1

In the formula, R¹, R², R³, R⁴, R⁵, A and A¹ are as defined above, Bocrepresents a t-butoxycarbonyl group, and L represents a leaving group.The leaving group represented by L is, for example, a halogen atom orthe like.

Production Method at [Step a]

The compound represented by the general formula (2-3) can be producedfrom the compound represented by the general formula (2-4), which isproduced according to Intermediate Production Method 1 below or theproduction method described in WO 2014/157600, according to the methoddescribed in Greene's Protective Groups in Organic Synthesis (John Wiley& Sons Inc.).

Production Method at [Step b]

The compound represented by the general formula (2-2) can be produced byreacting the compound represented by the general formula (2-3) with anoxidizing agent in an inert solvent.

Examples of the oxidizing agent used in this step include peroxides suchas a hydrogen peroxide solution, perbenzoic acid andm-chloroperoxybenzoic acid. The amount of the oxidizing agent used isselected as appropriate from the range of a 2- to 5-fold molar amountrelative to the compound represented by the general formula (2-3).

The inert solvent used in this reaction may be any solvent that does notmarkedly inhibit the reaction, and examples include aromatichydrocarbons such as benzene, toluene and xylene; halogenatedhydrocarbons such as methylene chloride and chloroform; halogenatedaromatic hydrocarbons such as chlorobenzene and dichlorobenzene;nitriles such as acetonitrile; esters such as ethyl acetate; organicacids such as formic acid and acetic acid; and polar solvents such aswater. One of these inert solvents may be used alone, and also two ormore of them may be used as a mixture.

The reaction temperature in this reaction is appropriately selected fromthe range of −10° C. to the reflux temperature of the inert solventused. The reaction time varies with the reaction scale, the reactiontemperature and the like and is not the same in every case, but isbasically selected as appropriate from the range of a few minutes to 48hours. After the reaction is completed, the resulting oxide is isolatedfrom the post-reaction mixture by the usual method. As needed,recrystallization, column chromatography, etc. can be employed for thepurification of the compound of interest.

Production Method at [Step c]

The compound represented by the general formula (2-1) can be producedfrom the compound represented by the general formula (2-2) according tothe method described in Greene's Protective Groups in Organic Synthesis(John Wiley & Sons Inc.).

Production Method at [Step d]

The compound represented by the general formula (1-1) can be produced byreacting the compound represented by the general formula (2-1) with ahalogenating agent in an inactive solvent.

Examples of the halogenating (chlorinating, brominating or iodinating)agent used in this step include halogen molecules such as chlorine,bromine or iodine molecules; halogenating agents such as thionylchloride, sulfuryl chloride, phosphorus oxychloride and phosphorustribromide; succinimides such as N-chlorosuccinimide (NCS),N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS); and hydantoinssuch as 1,3-dibromo-5,5-dimethylhydantoin (DBH) and1,3-diiodo-5,5-dimethylhydantoin (DIH). The amount of the halogenatingagent used is appropriately selected from the range of a 1- to 5-foldmolar amount relative to the compound represented by the general formula(2-1).

The inert solvent used in the halogenation (chlorination, bromination oriodination) may be any solvent that does not markedly inhibit thereaction, and examples include aromatic hydrocarbons such as benzene,toluene and xylene; halogenated hydrocarbons such as methylene chlorideand chloroform; halogenated aromatic hydrocarbons such as chlorobenzeneand dichlorobenzene; nitriles such as acetonitrile; esters such as ethylacetate; organic acids such as formic acid and acetic acid; and polarsolvents such as water. One of these inert solvents may be used alone,and also two or more of them may be used as a mixture.

The temperature for the halogenation is appropriately selected from therange of −10° C. to the reflux temperature of the inert solvent used.The reaction time varies with the reaction scale, the reactiontemperature and the like and is not the same in every case, but isbasically selected as appropriate from the range of a few minutes to 48hours. After the reaction is completed, the resulting oxide is isolatedfrom the post-reaction mixture by the usual method. As needed,recrystallization, column chromatography, etc. can be employed for thepurification of the compound of interest.

Production Method at [Step e]

The 1H-pyrrolo-condensed heterocyclic compound represented by thegeneral formula (1) can be produced by reacting the compound representedby the general formula (1-1) with R²-L in the presence of a base in aninert solvent.

The organic solvent used in this reaction may be any organic solventinert for the reaction. Examples of the organic solvent include ethersolvents such as dioxane, 1,2-dimethoxyethane and tetrahydrofuran;aromatic hydrocarbon solvents such as toluene, benzene and xylene; amidesolvents such as N,N-dimethylformamide, N,N-dimethylacetamide andN-methylpyrrolidone; and a mixed solvent of two or more kinds of them.

Examples of the base that can be used include inorganic bases such assodium hydroxide, potassium hydroxide, calcium hydroxide, bariumhydroxide, sodium carbonate, potassium carbonate, potassium hydrogencarbonate, sodium hydrogen carbonate, cesium carbonate and potassiumphosphate; alkoxides such as potassium t-butoxide, sodium methoxide andsodium ethoxide; alkali metal hydrides such as sodium hydride andpotassium hydride; and amines such as triethylamine, pyridine andpiperidine. The amount of the base used is usually 1 to 10 molarequivalents relative to 1 mol of the compound represented by the generalformula (1-1).

Since this reaction is an equimolar reaction of the reactants, thecompound represented by the general formula (1-1) and R²-L are usedbasically in equimolar amounts, but either of them may be used in anexcess amount.

The reaction temperature is usually in the range of room temperature tothe boiling point of the solvent used. The reaction time is usually afew minutes to dozens of hours. The reaction is preferably performedunder the atmosphere of an inert gas. After the reaction is completed,the compound of interest is isolated from the post-reaction mixture bythe usual method. As needed, recrystallization, column chromatography,etc. can be employed for the purification of the compound of interest.

In the case where the compound of interest is the compound of thegeneral formula (1-1) in which R¹ is an alkyl group, the compound of thegeneral formula (1-1) in which R¹ is an iodine atom, a bromine atom or achlorine atom is subjected to what is called the Negishi coupling(Aldrichimica Acta 2005, 38, 71) to yield the compound of interest. Inthe case where the compound of interest is the compound of the generalformula (1-1) in which R¹ is an alkoxycarbonyl group or an alkylcarbonylgroup, the compound of the general formula (1-1) in which R¹ is aniodine atom, a bromine atom or a chlorine atom is subjected to what iscalled the Mizoroki-Heck reaction (Modern Arylation Methods, Wiley-VCH)to yield the compound of interest.

In the case where the compound of interest is the compound of thegeneral formula (1-1) in which R¹ is a fluorine atom, the compound ofthe general formula (1-1) produced in Step d in which R¹ is an iodineatom, a bromine atom or a chlorine atom is reacted with a fluorinatingagent in the presence of a base in an inert solvent to yield thecompound of interest.

Examples of the fluorinating agent that can be used in this reactioninclude N-fluoro-N′-(chloromethyl)triethylenediaminebis(tetrafluoroborate), Selectfluor, (PhSO₂)₂NF and N-fluoropyridiniumtriflate. Preferred is Selectfluor. The amount of the fluorinating agentused is usually a 1 to 5 molar equivalents relative to 1 mol of thecompound of the general formula (1-1) in which R¹ is an iodine atom, abromine atom or a chlorine atom.

Examples of the base that can be used in the fluorination includeinorganic bases such as sodium hydroxide, potassium hydroxide, calciumhydroxide, barium hydroxide, sodium carbonate, potassium carbonate,potassium hydrogen carbonate, sodium hydrogen carbonate and cesiumcarbonate; and amines such as triethylamine, pyridine and piperidine.The amount of the base used is usually a 1 to 10 molar equivalentsrelative to 1 mol of the compound represented by the general formula(1-1).

The organic solvent used in the fluorination is not particularly limitedand may be any organic solvent inert for the reaction. Examples of theorganic solvent include nitrile solvents such as acetonitrile andbenzonitrile; water; and a mixed solvent of two or more kinds of them.

The reaction temperature in this reaction is usually in the range of−20° C. to the boiling point of the solvent used. The reaction time isusually a few minutes to dozens of hours. After the reaction iscompleted, the post-reaction mixture containing the compound of interestis treated with a reducing agent such as sodium thiosulfate, and thenthe compound of interest is isolated therefrom by the usual method. Asneeded, recrystallization, column chromatography, etc. can be employedfor the purification of the compound of interest.

The compound of the general formula (1-1) in which R¹ is an alkyl group,a fluorine atom, an alkoxycarbonyl group or an alkylcarbonyl group canbe converted into the corresponding 1H-pyrrolo-condensed heterocycliccompound represented by the general formula (1) according to theproduction method at [Step e].

Intermediate Production Method

In the formula, R¹, R², R³, R⁴, R⁵, A¹ and A³ are as defined above, Xrepresents a halogen atom, and R represents a tertiary alkyl group suchas a t-butyl group and a 1-phenyl-2-methylpropyl-2-yl group.

Production Method at [Step a]

The β-ketoester compound represented by the general formula (3-3)produced by Claisen condensation (Org. React. 1942, 1, 266) of anaromatic carboxylic acid ester and an acetic acid ester and esterexchange is reacted with the halogenated nitro compound represented bythe general formula (4) in the presence of a base in an inert solvent toyield the compound represented by the general formula (3-2).

The organic solvent used is not particularly limited and may be anyorganic solvent inert for the reaction. Examples of the organic solventinclude ether solvents such as dioxane, 1,2-dimethoxyethane andtetrahydrofuran; aromatic hydrocarbon solvents such as toluene, benzeneand xylene; amide solvents such as N,N-dimethylformamide,N,N-dimethylacetamide and N-methylpyrrolidone; and a mixed solvent oftwo or more kinds of them.

Examples of the base that can be used include inorganic bases such assodium hydroxide, potassium hydroxide, calcium hydroxide, bariumhydroxide, sodium carbonate, potassium carbonate, potassium hydrogencarbonate, sodium hydrogen carbonate, cesium carbonate and potassiumphosphate; alkoxides such as potassium t-butoxide, sodium methoxide andsodium ethoxide; alkali metal hydrides such as sodium hydride andpotassium hydride; and amines such as triethylamine, pyridine andpiperidine. The amount of the base used is usually 1 to 10 molarequivalents relative to 1 mol of compound (3-3).

Since this reaction is an equimolar reaction of the reactants, compound(3-3) and compound (4) are used basically in equimolar amounts, buteither of them may be used in an excess amount.

The reaction temperature is usually in the range of room temperature tothe boiling point of the solvent used. The reaction time is usually afew minutes to dozens of hours. The reaction is preferably performedunder the atmosphere of an inert gas. After the reaction is completed,the compound of interest is isolated from the post-reaction mixture bythe usual method. As needed, recrystallization, column chromatography,etc. can be employed for the purification of the compound of interest.

Production Method at [Step β]

The compound represented by the general formula (3-1) can be produced bytreating the compound represented by the general formula (3-2) with anacid in the presence or absence of a solvent.

Examples of the acid used in this reaction include inorganic acids suchas hydrochloric acid, sulfuric acid and nitric acid; organic acids suchas formic acid, acetic acid, propionic acid, trifluoroacetic acid andbenzoic acid; and sulfonic acids such as methanesulfonic acid andtrifluoromethanesulfonic acid. The amount of the acid used isappropriately selected from the range of a 1- to 10-fold molar amountrelative to the ester compound represented by the general formula (3-2).In some cases, the acid can be used also as the solvent for thisreaction.

The inert solvent used in this reaction may be any solvent that does notmarkedly inhibit the progress of the reaction, and examples includearomatic hydrocarbons such as benzene, toluene and xylene; halogenatedhydrocarbons such as methylene chloride, chloroform and carbontetrachloride; halogenated aromatic hydrocarbons such as chlorobenzeneand dichlorobenzene; amides such as dimethylformamide anddimethylacetamide; ketones such as acetone and methyl ethyl ketone; andpolar solvents such as 1,3-dimethyl-2-imidazolidinone. One of theseinert solvents may be used alone, and also two or more of them may beused as a mixture. In the case where the acid is used also as thesolvent, it is not necessary to use another solvent.

The reaction temperature may be in the range of room temperature to theboiling point of the inert solvent used. The reaction time varies withthe reaction scale and the reaction temperature, but is basically in therange of a few minutes to 48 hours.

After the reaction is completed, the compound of interest is isolatedfrom the post-reaction mixture by the usual method. As needed,recrystallization, column chromatography, etc. can be employed for thepurification of the compound of interest.

Production Method at [Step γ]

The reaction in this step is reduction and dehydration of the nitrocompound represented by the general formula (3-1) to produce the1H-pyrrolo-condensed heterocyclic compound represented by the generalformula (2-4).

For the reduction, the conditions for reduction of nitro groupsdescribed in the known literature (see “New Lecture of ExperimentalChemistry (Shin Jikken Kagaku Kouza)”, vol. 15, Oxidation and ReductionII, 1977, edited by the Chemical Society of Japan, published by Maruzen)can be used.

Examples of the inert solvent that can be used in this reaction includealcohols such as methanol and ethanol; ethers such as tetrahydrofuranand dioxane; organic acids such as formic acid and acetic acid; andwater. One of these inert solvents may be used alone, and also two ormore of them may be used as a mixture. An aqueous solution of an acidused as the reducing agent in this reaction can be used also as theinert solvent for the reaction.

Examples of the reducing agent that can be used in this reaction includemetal-acid and metal-salt. Examples of the metal include iron, tin andzinc, examples of the acid include inorganic acids such as hydrochloricacid and sulfuric acid and organic acids such as acetic acid, andexamples of the salt include tin chloride and ammonium chloride. Inaddition, the metal may be a combination of two or more of theseexamples, and the same applies to the acid and the salt. As for theamount of the reducing agent used, the amount of the metal isappropriately selected from the range of an about 1- to 10-fold molaramount relative to the nitro compound represented by the general formula(3-1), and the amount of the acid or the salt is appropriately selectedfrom the range of an about 0.05- to 10-fold molar amount relative to thenitro compound represented by the general formula (3-1). The reactiontemperature can be selected from the range of about 0 to 150° C. Thereaction time varies with the reaction scale, the reaction temperatureand the like, but is basically selected as appropriate from the range ofa few minutes to about 48 hours. The reduction in this step can also beperformed by catalytic hydrogenation in the presence of a catalyst.Examples of the catalyst include palladium carbon. After the reaction iscompleted, the compound of interest is isolated from the post-reactionmixture by the usual method. As needed, recrystallization, distillation,column chromatography, etc. can be employed for the purification of thecompound of interest. The 1H-pyrrolo-condensed heterocyclic compoundrepresented by the general formula (2-4) produced according to theproduction scheme described above is subjected to the reactions inProduction Method 1 to yield the 1H-pyrrolo-condensed heterocycliccompound represented by the general formula (1). The intermediatecompound can also be produced according to the production methoddescribed in WO 2014/157600.

Specific examples of the compound of the present invention are shownbelow. In the tables given below, Me stands for a methyl group, Etstands for an ethyl group, n-Pr stands for a n-propyl group, i-Pr standsfor an isopropyl group, c-Pr stands for a cyclopropyl group, and t-Bustands for a tert-butyl group. Ph stands for a phenyl group, Bn standsfor a benzyl group, Pyrazol stands for a pyrazolyl group, Pyrrol standsfor a pyrrolyl group, Triazol stands for a triazolyl group, Thienylstands for a thienyl group, and Pyridyl stands for a pyridyl group. Acstands for an acetyl group.

Shown in the column of “Physical property” is a melting point (° C.), arefractive index (° C.) or “NMR”. ¹H-NMR data are shown in Tables 20 to22.

TABLE 1 Compound Physical No. R¹ R² R³ R⁴ m property 1-1 F H CF₃ H 2 1-2F H CF₃ Cl 2 1-3 F H CF₃ I 2 127-128 1-4 F H CF₃ c-Pr 2 NMR 1-5 F H CF₃i-Pr 2 1-6 F H CF₃ 3-F—Ph 2 1-7 F H CF₃ 4-F—Ph 2 234-235 1-8 F H CF₃3-CF₃—Ph 2 NMR 1-9 F H CF₃ 4-CF₃—Ph 2 1-10 F H CF₃ 3-Cl—Ph 2 1-11 F HCF₃ 4-Cl—Ph 2 1-12 F H CF₃ 2-OCF₃—Ph 2 1-13 F H CF₃ 3-OCF₃—Ph 2 1-14 F HCF₃ 4-OCF₃—Ph 2 1-15 F H CF₃ CHO 2 1-16 F H CF₃ CH═NOH 2 1-17 F H CF₃CH═NOCH₂CHF₂ 2 1-18 F H CF₃ CH═NOCH₂CF₃ 2 1-19 F H CF₃ Ac 2 1-20 F H CF₃C(Me)═NOH 2 1-21 F H CF₃ C(Me)═NOCH₂CHF₂ 2 1-22 F H CF₃ C(Me)═NOCH₂CF₃ 21-23 F H CF₃ NH₂ 2 1-24 F H CF₃ NHCO₂-t-Bu 2 1-25 F H CF₃ NHAc 2A and A¹ each represent a nitrogen atom, and R⁵ represents a hydrogenatom.

TABLE 2 Com- pound Physical No. R¹ R² R³ R⁴ m property 1-26 F H CF₃ SMe2 1-27 F H CF₃ SO₂Me 2 1-28 F H CF₃ SEt 2 1-29 F H CF₃ SO₂Et 2 1-30 F HCF₃ SCF₃ 2 1-31 F H CF₃ 1-Me-Pyrazol-3-yl 2 1-32 F H CF₃1-CHF₂-Pyrazol-3-yl 2 1-33 F H CF₃ 1-Me-5-OMe-Pyrazol-3-yl 2 1-34 F HCF₃ 1-Me-5-OCHF₂-Pyrazol-3-yl 2 1-35 F H CF₃ 3-OCHF₂-Pyrazol-1-yl 2 1-36F H CF₃ 3-Br-Pyrrol-1-yl 2 1-37 F H CF₃ 1,2,4-Triazol-1-yl 2 1-38 Cl HCF₃ H 2 1-39 Cl H CF₃ Cl 2 1-40 Cl H CF₃ I 2 190-191 1-41 Cl H CF₃ c-Pr2 205-206 1-42 Cl H CF₃ i-Pr 2 1-43 Cl H CF₃ 3-F—Ph 2 1-44 Cl H CF₃4-F—Ph 2 154-155 1-45 Cl H CF₃ 3-CF₃—Ph 2 244-245 1-46 Cl H CF₃ 4-CF₃—Ph2 212-213 1-47 Cl H CF₃ 3-Cl—Ph 2 1-48 Cl H CF₃ 4-Cl—Ph 2 NMR 1-49 Cl HCF₃ 2-OCF₃—Ph 2 1-50 Cl H CF₃ 3-OCF₃—Ph 2 122-124A and A¹ each represent a nitrogen atom, and R⁵ represents a hydrogenatom.

TABLE 3 Com- pound Physical No. R¹ R² R³ R⁴ m property 1-51 Cl H CF₃4-OCF₃—Ph 2 1-52 Cl H CF₃ CHO 2 1-53 Cl H CF₃ CH═NOH 2 1-54 Cl H CF₃CH═NOCH₂CHF₂ 2 1-55 Cl H CF₃ CH═NOCO₂CF₃ 2 1-56 Cl H CF₃ Ac 2 1-57 Cl HCF₃ C(Me)═NOH 2 1-58 Cl H CF₃ C(Me)═NOCH₂CHF₂ 2 1-59 Cl H CF₃C(Me)═NOCH₂CF₃ 2 1-60 Cl H CF₃ NH₂ 2 1-61 Cl H CF₃ NHCO₂-t-Bu 2 1-62 ClH CF₃ NHAc 2 1-63 Cl H CF₃ SMe 2 1-64 Cl H CF₃ SO₂Me 2 1-65 Cl H CF₃ SEt2 1-66 Cl H CF₃ SO₂Et 2 1-67 Cl H CF₃ SCF₃ 2 1-68 Cl H CF₃1-Me-Pyrazol-3-yl 2 1-69 Cl H CF₃ 1-CHF₂-Pyrazol-3-yl 2 1-70 Cl H CF₃1-Me-5-OMe-Pyrazol-3-yl 2 1-71 Cl H CF₃ 1-Me-5-OCHF₂-Pyrazol-3-yl 2 1-72Cl H CF₃ 3-OCHF₂-Pyrazol-1-yl 2 1-73 Cl H CF₃ 3-Br-Pyrrol-1-yl 2 1-74 ClH CF₃ 1,2,4-Triazol-1-yl 2A and A¹ each represent a nitrogen atom, and R⁵ represents a hydrogenatom.

TABLE 4 Compound Physical No. R¹ R² R³ R⁴ m property 1-75 F H CF₃ CF₃ 2182-183 1-76 Cl H CF₃ CF₃ 3 215-216 1-77 Br H CF₃ CF₃ 2 205-206 1-78 I HCF₃ CF₃ 2 227-228 1-79 Me H CF₃ CF₃ 2 151-152 1-80 CN H CF₃ CF₃ 0 NMR1-81 CO₂Me H CF₃ CF₃ 0 NMR 1-82 CO₂Et H CF₃ CF₃ 0 NMR 1-83 Br H CF₃ I 21-84 I H CF₃ I 2 1-85 Me H CF₃ I 2 1-86 CN H CF₃ I 2 1-87 CO₂Me H CF₃ I2 1-88 CO₂Et H CF₃ I 2 1-89 Br H CF₃ c-Pr 2 1-90 I H CF₃ c-Pr 2 1-91 MeH CF₃ c-Pr 2 1-92 CN H CF₃ c-Pr 2 1-93 CO₂Me H CF₃ c-Pr 2 1-94 CO₂Et HCF₃ c-Pr 2 1-95 Cl H CF₃ Cl 0 142-143 1-96 Br H CF₃ CF₃ 1 NMR 1-97 I HCF₃ CF₃ 1 NMR 1-98 CH═CH₂ H CF₃ CF₃ 2 172-173A and A¹ each represent a nitrogen atom, and R⁵ represents a hydrogenatom.

TABLE 5 Com- pound Physical No. R¹ R² R³ R⁴ m property 1-99 Cl H CF₃OCH₂CF₃ 2 149-152 1-100 Cl H CF₃ 4-CF₃-BnO 2 193-195 1-101 Cl H CF₃3-CF₃-pyrazole-1-yl 2 137-141 1-102 Me H CF₃ 4-F—Ph 2 224-225 1-103 Cl HCF₃ 2-CF₃—Ph 2 252-253 1-104 Cl H CF₃ 3,5-F₂—Ph 2 272-273 1-105 Cl H CF₃3-Cl—Ph 2 244-245 1-106 Cl H CF₃ 2,4,5-Cl₃-Thien-3-yl 2 95-96 1-107 Cl HCF₃ 3-Pyridyl 2 285-286 1-108 Cl H CF₃ CH═NOCH₂CF₃ 2 114-115 (E-isomer)1-109 Cl H CF₃ CH═NOCH₂CF₃ 2 1.5481(22° (Z-isomer) C.) 1-110 F H CF₃CH═NOCH₂CF₃ 2 152-153 (E-isomer) 1-111 OH H CF₃ CH═NOCH₂CF₃ 2 141-142(E-isomer) 1-112 Cl H CF₃ OEt 2 201-203 1-113 CH₂NMe₂ H CF₃ 4-F—Ph 2192-193 1-114 F H CF₃ 3,5-F₂—Ph 2 250-251 1-115 Cl H CF₃ 3-CN—Ph 2262-263 1-116 F H CF₃ OCH₂CF₃ 2 1-117 F H CF₃ O-4-CF³⁻Bn 2 1-118 F H CF₃3-CF₃-Pyrazol-1-yl 2 1-119 Br H CF₃ 4-F—Ph 2 1-120 CN H CF₃ 3-CF₃—Ph 2233-234 1-121 Cl H CF₃ 3-Me-4-F—Ph 2 114-116 1-122 Cl H CF₃ 3-F-4-Cl—Ph2 267-270 1-123 Cl H CF₃ 3-Cl-4-F—Ph 2 222-224 1-124 Cl H CF₃2-F-5-CF₃—Ph 2 293-294 1-125 Cl H CF₃ 4-Et—Ph 2 119-120 1-126 Cl H CF₃3,4-F₂—Ph 2 218-219 1-127 Cl H CF₃ 3,4,5-F₃—Ph 2 251-252 1-128 Cl H CF₃4-CO₂Me—Ph 2 261-263 1-129 Cl H CF₃ 4-i-Pr—Ph 2 226-227 1-130 Cl H CF₃3-Cl-4-O-i-Pr—Ph 2 215-216A and A¹ each represent a nitrogen atom, and R⁵ represents a hydrogenatom.

TABLE 6 Compound Physical No. R¹ R² R³ R⁵ m property 2-1 F H CF₃ H 2 2-2F H CF₃ Cl 2 2-3 F H CF₃ I 2 2-4 F H CF₃ c-Pr 2 2-5 F H CF₃ i-Pr 2 2-6 FH CF₃ 3-F—Ph 2 2-7 F H CF₃ 4-F—Ph 2 2-8 F H CF₃ 3-CF₃—Ph 2 2-9 F H CF₃4-CF₃—Ph 2 2-10 F H CF₃ 3-Cl—Ph 2 2-11 F H CF₃ 4-Cl—Ph 2 2-12 F H CF₃2-OCF₃—Ph 2 2-13 F H CF₃ 3-OCF₃—Ph 2 2-14 F H CF₃ 4-OCF₃—Ph 2 2-15 F HCF₃ CHO 2 2-16 F H CF₃ CH═NOH 2 2-17 F H CF₃ CH═NOCH₂CHF₂ 2 2-18 F H CF₃CH═NOCH₂CF₃ 2 2-19 F H CF₃ Ac 2 2-20 F H CF₃ C(Me)═NOH 2 2-21 F H CF₃C(Me)═NOCH₂CHF₂ 2 2-22 F H CF₃ C(Me)═NOCH₂CF₃ 2 2-23 F H CF₃ NH₂ 2 2-24F H CF₃ NHCO₂-t-Bu 2 2-25 F H CF₃ NHAc 2A and A¹ each represent a nitrogen atom, and R⁴ represents a hydrogenatom.

TABLE 7 Com- pound Physical No. R¹ R² R³ R⁵ m property 2-26 F H CF₃ SMe2 2-27 F H CF₃ SO₂Me 2 2-28 F H CF₃ SEt 2 2-29 F H CF₃ SO₂Et 2 2-30 F HCF₃ SCF₃ 2 2-31 F H CF₃ 1-Me-Pyrazol-3-yl 2 2-32 F H CF₃1-CHF₂-Pyrazol-3-yl 2 2-33 F H CF₃ 1-Me-5-OMe-Pyrazol-3-yl 2 2-34 F HCF₃ 1-Me-5-OCHF₂-Pyrazol-3-yl 2 2-35 F H CF₃ 3-OCHF₂-Pyrazol-1-yl 2 2-36F H CF₃ 3-Br-Pyrrol-1-yl 2 2-37 F H CF₃ 1,2,4-Triazol-1-yl 2 2-38 Cl HCF₃ H 2 2-39 Cl H CF₃ Cl 2 2-40 Cl H CF₃ I 2 2-41 Cl H CF₃ c-Pr 2 2-42Cl H CF₃ i-Pr 2 2-43 Cl H CF₃ 3-F—Ph 2 2-44 Cl H CF₃ 4-F—Ph 2 2-45 Cl HCF₃ 3-CF₃—Ph 2 2-46 Cl H CF₃ 4-CF₃—Ph 2 2-47 Cl H CF₃ 3-Cl—Ph 2 2-48 ClH CF₃ 4-Cl—Ph 2 2-49 Cl H CF₃ 2-OCF₃—Ph 2 2-50 Cl H CF₃ 3-OCF₃—Ph 2A and A¹ each represent a nitrogen atom, and R⁴ represents a hydrogenatom.

TABLE 8 Com- pound Physical No. R¹ R² R³ R⁵ m property 2-51 Cl H CF₃4-OCF₃—Ph 2 2-52 Cl H CF₃ CHO 2 2-53 Cl H CF₃ CH═NOH 2 2-54 Cl H CF₃CH═NOCH₂CHF₂ 2 2-55 Cl H CF₃ CH═NOCH₂CF₃ 2 2-56 Cl H CF₃ Ac 2 2-57 Cl HCF₃ C(Me)═NOH 2 2-58 Cl H CF₃ C(Me)═NOCH₂CHF₂ 2 2-59 Cl H CF₃C(Me)═NOCH₂CF₃ 2 2-60 Cl H CF₃ NH₂ 2 2-61 Cl H CF₃ NHCO₂-t-Bu 2 2-62 ClH CF₃ NHAc 2 2-63 Cl H CF₃ SMe 2 2-64 Cl H CF₃ SO₂Me 2 2-65 Cl H CF₃ SEt2 2-66 Cl H CF₃ SO₂Et 2 2-67 Cl H CF₃ SCF₃ 2 2-68 Cl H CF₃1-Me-Pyrazol-3-yl 2 2-69 Cl H CF₃ 1-CHF₂-Pyrazol-3-yl 2 2-70 Cl H CF₃1-Me-5-OMe-Pyrazol-3-yl 2 2-71 Cl H CF₃ 1-Me-5-OCHF₂-Pyrazol-3-yl 2 2-72Cl H CF₃ 3-OCHF₂-Pyrazol-1-yl 2 2-73 Cl H CF₃ 3-Br-Pyrrol-1-yl 2 2-74 ClH CF₃ 1,2,4-Triazol-1-yl 2 256-257A and A¹ each represent a nitrogen atom, and R⁴ represents a hydrogenatom.

TABLE 9 Compound Physical No. R¹ R² R³ R⁵ m property 2-75 Br H CF₃ CF₃ 22-76 I H CF₃ CF₃ 2 2-77 Me H CF₃ CF₃ 2 2-78 CN H CF₃ CF₃ 0 2-79 CO₂Me HCF₃ CF₃ 0 2-80 CO₂Et H CF₃ CF₃ 0 2-81 Br H CF₃ I 2 2-82 I H CF₃ I 2 2-83Me H CF₃ I 2 2-84 CN H CF₃ I 2 2-85 CO₂Me H CF₃ I 2 2-86 CO₂Et H CF₃ I 22-87 Br H CF₃ c-Pr 2 2-88 I H CF₃ c-Pr 2 2-89 Me H CF₃ c-Pr 2 2-90 CN HCF₃ c-Pr 2 2-91 CO₂Me H CF₃ c-Pr 2 2-92 CO₂Et H CF₃ c-Pr 2 2-93 Cl H CF₃Cl 0 142-143A and A¹ each represent a nitrogen atom, and R⁴ represents a hydrogenatom.

TABLE 10 Compound Physical No. R¹ R² R³ R⁴ R⁵ m property 3-1 CH═CH₂CO₂-t-Bu CF₃ CF₃ H 2 NMR 3-2 Br CO₂-t-Bu CF₃ CF₃ H 2 NMR 3-3 Cl Ac CF₃ IH 2 180-181 3-4 Cl Me CF₃ I H 2 293-294 3-5 Cl Me CF₃ c-Pr H 2 254-255A and A¹ each represent a nitrogen atom.

TABLE 11 Compound Physical No. R¹ R² R³ R⁴ R⁵ m property 3-6 Br CO₂-t-BuCF₃ 4-F—Ph H 2 172-173 3-7 Cl CH₂CF₃ CF₃ CH═NOCH₂CF₃ H 2 1.4569(21° C.)(E-isomer) 3-8 F Ac CF₃ CH═NOCH₂CF₃ H 2 1.4612(21° C.) (E-isomer) 3-9 FAc CF₃ 3-CF₃—Ph H 2 75-76 3-10 F Ac CF₃ 4-F—Ph H 2 75-76 3-11 Cl Ac CF₃3-CN—Ph H 2 95-96 3-12 Br CO₂-t-Bu CF₃ 4-F—Ph H 2 172-173 3-13 Cl Ac CF₃OCH₂CF₃ H 2 235-237 3-14 Cl CH₂OMe CF₃ 4-F—Ph H 2 194-195 3-15 Cl CH₂SMeCF₃ 4-F—Ph H 2 65-66 3-16 CN CO₂-t-Bu CF₃ I H 2 161-162 3-17 Cl CH₂OMeCF₃ 3-CF₃—Ph H 2 90-92 3-18 F CH₂CF₃ CF₃ 3-CF₃—Ph H 2 127-128 3-19 FCH₂CHF₂ CF₃ 3-CF₃—Ph H 2 92-95 3-20 F CH₂C≡CH CF₃ 3-CF₃—Ph H 2 NMR 3-21F CH₂CH═CH CF₃ 3-CF₃—Ph H 2 NMR 3-22 F CH₂-c-Pr CF₃ 3-CF₃—Ph H 2 70-713-23 F CO₂Me CF₃ 3-CF₃—Ph H 2 3-24 F CH₂OMe CF₃ 3-CF₃—Ph H 2 NMR 3-25 FCH₂OEt CF₃ 3-CF₃—Ph H 2 NMR 3-26 Cl CH₂CF₃ CF₃ 3-CF₃—Ph H 2 3-27 ClCH₂CHF₂ CF₃ 3-CF₃—Ph H 2 92-95 3-28 F CH₂OEt CF₃ 4-F—Ph H 2 3-29 Cl AcCF₃ 4-CO₂Me—Ph H 2 117-119 3-30 Cl Ac CF₃ 4-i-Pr—Ph H 2  99-100 3-31 ClAc CF₃ 3-Cl-4-O-i-Pr—Ph H 2 108-109A and A¹ each represent a nitrogen atom.

TABLE 12 Com- pound Physical No. R¹ R² R³ R⁴ R⁵ m property 3-32 Cl AcCF₃ c-Pr H 2 199-200 3-33 Cl EtCO CF₃ c-Pr H 2 3-34 Cl i-PrCO CF₃ c-Pr H2 3-35 Cl CO₂Me CF₃ c-Pr H 2 3-36 Cl CO₂Et CF₃ c-Pr H 2 3-37 Cl CH₂OMeCF₃ c-Pr H 2 1.4715(25° C.) 3-38 Cl CH₂OEt CF₃ c-Pr H 2 3-39 Cl CH₂CF₃CF₃ c-Pr H 2 3-40 Cl CH₂CHF₂ CF₃ c-Pr H 2 77-78 3-41 Cl CH₂C≡CH CF₃ c-PrH 2 3-42 Cl CH₂CH═CH₂ CF₃ c-Pr H 2 3-43 Cl CH₂-c-Pr CF₃ c-Pr H 2 3-44 FAc CF₃ c-Pr H 2 129-130 3-45 F EtCO CF₃ c-Pr H 2 124-125 3-46 F i-PrCOCF₃ c-Pr H 2 1.4512(21° C.) 3-47 F CO₂Me CF₃ c-Pr H 2 1.4165(21° C.)3-48 F CO₂Et CF₃ c-Pr H 2 1.3940(21° C.) 3-49 F CH₂OMe CF₃ c-Pr H 21.4673(21° C.) 3-50 F CH₂OEt CF₃ c-Pr H 2 1.3618(21° C.) 3-51 F CH₂CF₃CF₃ c-Pr H 2 1.3875(21° C.) 3-52 F CH₂CHF₂ CF₃ c-Pr H 2 127-128 3-53 FCH₂C≡CH CF₃ c-Pr H 2 130-131 3-54 F CH₂CH═CH₂ CF₃ c-Pr H 2 1.4369(21°C.) 3-55 F CH₂-c-Pr CF₃ c-Pr H 2 1.4863(21° C.)A and A¹ each represent a nitrogen atom.

TABLE 13 Compound Physical No. R¹ R² R³ R⁴ R⁵ m property 4-1 F CO₂-t-BuCF₃ CF₃ H 2 NMRA represents an N-oxide and A¹ represents a nitrogen atom.

TABLE 14 Compound Physical No. R¹ R² R³ R⁴ m property 5-1 Cl H CF₃ CF₃ 0151-152 5-2 Cl H CF3 I 0 153-154 5-3 Cl CO₂-t-Bu CF3 I 0 159-160 5-4 ClH CF3 I 2 160-161 5-5 Cl H CF3 4-F—Ph 2 5-6 Cl H CF3 3-CF₃—Ph 2A represents CH, A¹ represents a nitrogen atom, and R⁵ represents ahydrogen atom.

TABLE 15 Compound Physical No. R³ R⁴ R⁵ m property 6-1 CF₃ I H 0 164-1656-2 CF₃ c-Pr H 0 165-166 6-3 CF₃ H Cl 2 171-172 6-4 CF₃ 3-CF₃—Ph H 0104-105 6-5 CF₃ I H 2 222-223 6-6 CF₃ CF₃ H 2 171-172 6-7 CF₃1,2,4-Triazol-1-yl H 2 245-246 6-8 CF₃ 4-F—Ph H 2 239-241 6-9 CF₃ c-Pr H2 137-138 6-10 CF₃ 4-CF₃—Ph H 2 220-221 6-11 CF₃ H 3-F—Ph 2 NMR 6-12 CF₃H 4-F—Ph 2 132-133 6-13 CF₃ 4-Cl—Ph H 2 240-241A and A¹ each represent a nitrogen atom, and R¹ and R² each represent ahydrogen atom.

TABLE 16 Com- pound Physical No. R³ R⁴ R⁵ m property 6-14 CF₃ OEt H 2211-213 6-15 CF₃ OCH₂CF₃ H 2 219-220 6-16 CF₃ 4-CF₃-BnO H 2 220-221 6-17CF₃ 3-CF₃—PhO H 2 154-155 6-18 CF₃ 3-F—PhO H 2 198-201 6-19 CF₃ 2-CF₃—PhH 2 122-123 6-20 CF₃ 3,5-F₂—Ph H 2 119-120 6-21 CF₃ 3-Cl—Ph H 2 117-1186-22 CF₃ 3-Thienyl H 2 143-144 6-23 CF₃ 3-Pyridyl H 2 240-241 6-24 CF₃3-CN—Ph H 2 258-259 6-25 CF₃ 3-OCF₃—Ph H 2 156-158 6-26 CF₃ 3-Me-4-F—PhH 2 175-177 6-27 CF₃ H 1,2,4-triazol-1-yl 2 251-252 6-28 CF₃2-F-5-CF₃—Ph H 2 230-231 6-29 CF₃ 4-Et—Ph H 2 106-108 6-30 CF₃ 3,4-F₂—PhH 2 235-236 6-31 CF₃ 3,4,5-F₃—Ph H 2 226-228 6-32 CF₃ Pyrazol-1-yl H 2269-270 6-33 CF₃ 3-Me-Pyrazol-1-yl H 2 256-257 6-34 CF₃ 4-CO₂Me—Ph H 2297-299 6-35 CF₃ 4-i-Pr—Ph H 2 212-214 6-36 CF₃ 4-O-i-Pr—Ph H 2 252-2546-37 CF₃ 3-F—Ph H 2A and A¹ each represent a nitrogen atom, and R¹ and R² each represent ahydrogen atom.

TABLE 17 Compound Physical No. R¹ R² R³ R⁴ R⁵ m property 7-1 H CH₂CF₃CF₃ H CH═NOCH₂CF₃ 0 NMR (E-isomer) 7-2 H CH₂CF₃ CF₃ H CH═NOCH₂CF₃ 1 NMR(E-isomer) 7-3 H CH₂CF₃ CF₃ H CH═NOCH₂CF₃ 2 NMR (E-isomer) 7-4 HCO₂-t-Bu CF₃ 3-CF₃—Ph H 0 NMR 7-5 H CO₂-t-Bu CF₃ I H 0 155-156 7-6 HCO₂-t-Bu CF₃ I H 2 168-169 7-7 H CO₂-t-Bu CF₃ 3-CF₃—Ph H 2 NMR 7-8 HSO₂Et CF₃ CF₃ H 0 NMR 7-9 H SO₂Et CF₃ CF₃ H 2 220-221 7-10 H CO₂-t-BuCF₃ H Cl 0 NMR 7-11 H CO₂-t-Bu CF₃ H Cl 2 NMR 7-12 H CO₂-t-Bu CF3 H4-F—Ph 2 57-58 7-13 H CO₂-t-Bu CF3 H CH═NOCH₂CF₃ 2 70-71A and A¹ each represent a nitrogen atom.

TABLE 18 Compound Physical No. R¹ R² R³ R⁴ m property 8-1 H H CF₃ CF₃ 0168-169 8-2 H H CF₃ CF₃ 2 200-201 8-3 H CO₂-t-Bu CF₃ CF₃ 2 145-146 8-4 HH CF3 4-F—Ph 2 8-5 H H CF3 3-CF₃—Ph 2A represents CH, A¹ represents a nitrogen atom, and R⁵ represents ahydrogen atom.

TABLE 19 Compound Physical No. R¹ R² R³ R⁴ R⁵ m property 9-1 H CO₂-t-BuCF₃ I H 2 115-116 9-2 H CO₂-t-Bu CF₃ 3-CF₃—Ph H 2 NMR 9-3 H SO₂Et CF₃CF₃ H 2 NMR 9-4 H CO₂-t-Bu CF₃ H Cl 2 NMR 9-5 H H CF₃ CF₃ H 2 271-2729-6 H H CF₃ H Cl 2 231-232 9-7 H H CF₃ I H 2 269-270A represents an N-oxide and A¹ represents a nitrogen atom.

TABLE 20 ¹H - NMR Data Com- pound No. ¹H-NMR Data 1-4 10.1(1H, s),8.81(1H, d), 8.79(1H, d), 8.11(1H, d), 8.02(1H, d), 2.97(2H, q),2.09(1H, m), 1.26(2H, m), 1.19(3H, t), 0.95(2H, m) 1-8 10.3(1H, s),8.85(1H, d), 8.74(1H, d), 8.07(1H, d), 7.95(1H, d), 7.91(1H, d),7.79(1H, d), 7.72(1H, d), 3.07(2H, q), 1.25(3H, t) 1-48 10.1(1H, s),9.26(1H, d), 8.89(1H, d), 8.72(1H, d), 8.10(1H, d), 7.69(2H, d),7.57(1H, d), 2.88(2H, q), 1.18(3H, t) 1-80 10.43(1H, s), 8.94(1H, s),8.89(1H, s), 8.13(1H, s), 8.07(1H, s), 3.09(2H, dd), 1.38(3H, t) 1-819.61(1H, s), 8.93(1H, s), 8.70(1H, s), 8.03(1H, s), 7.90(1H, s),3.88(3H, s), 2.93(2H, dd), 1.26(3H, t) 1-82 9.16(1H, s), 8.98(1H, s),8.73(1H, s), 8.02(1H, s), 7.91(1H, s), 4.34(2H, dd), 2.92(2H, dd),1.25(3H, t), 1.21(3H, t) 1-96 11.7(1H, s), 9.13(1H, d), 8.86(1H, d),8.43(1H, d), 8.10(1H, d), 2.77(1H, m), 2.58(1H, m), 1.07(3H, t) 1-9711.7(1H, s), 9.16(1H, d), 8.87(1H, d), 8.41(1H, d), 8.07(1H, d),2.74(1H, m), 2.56(1H, m), 1.05(3H, t)

TABLE 21 Com- pound No. ¹H-NMR Data 3-1 9.25(1H, d), 8.90(1H, d),8.84(1H, s), 8.70(1H, d), 6.63(1H, dd), 6.18(1H, dd), 5.51(1H, dd),2.98(2H, q), 1.33(9H, s), 1.18(3H, t) 3-2 9.28(1H, d), 8.93(1H, d),8.90(1H, s), 8.70(1H, d), 3.10(2H, q), 1.33(9H, s), 1.28(3H, t) 3-209.29(1H, d), 8.83(1H, d), 8.71(1H, d), 8.21(1H, d), 7.99(1H, d), 7.94(1H, dd), 7.82(1H, dd), 7.75(1H, dd), 4.78(2H, br-d), 3.25(2H, q),2.40(1H, t), 1.33(3H, t) 3-21 9.26(1H, d), 8.80(1H, d), 8.71 (1H, d),8.00(1H, d), 7.98(1H, d), 7.94(1H, d), 7.82(1H, dd), 7.74(1H, d),5.94(1H, ddd), 5.19(1H, s), 5.18(1H, d), 4.64(2H, br-d), 3.30(2H, q),1.35(3H, t) 3-24 9.26(1H, d), 8.85(1H, d), 8.70(1H, d), 8.18(1H, d),7.97(1H, d), 7.93 (1H, d), 7.82(1H, dd), 7.75(1H, dd), 5.61(1H, d),5.09(1H, d), 3.24(3H, s), 3.23(2H, q), 1.33(3H, t) 3-25 9.26(1H, d),8.84(1H, d), 8.70(1H, d), 8.20(1H, d), 7.97(1H, d), 7.93 (1H, dd),7.82(1H, dd), 7.75(1H, d), 5.64(1H, d), 5.16(1H, d), 3.53-3.30(2H, m),3.24(2H, q)1.33(3H, t), 1.08(3H, t) 4-1 9.19(1H, d), 8.66(1H, d),8.51(1H, d), 8.45(1H, d), 7.18(1H, s), 3.08(2H, q), 1.32(9H, s),1.27(3H, t) 6-11 11.1(1H, s), 8.92(1H, s), 8.64(1H, d), 8.30(1H, s),8.07(1H, s), 7.97(1H, d), 7.95(1H, dd), 7.78(1H, td), 7.56(1H, td),3.18(2H, q), 1.24(3H, t)

TABLE 22 Com- pound No. ¹H-NMR Data 7-1 8.82(1H, d), 8.23(1H, s),7.97(1H, d), 7.83(1H, d), 7.73(1H, d), 7.35(1H, s), 5.16(2H, q),4.58(2H, q), 2.97(2H, q), 1.33(3H, t) 7-2 8.87(1H, d), 8.54(1H, d),8.33(1H, s), 8.10(1H, d), 8.01(1H, s), 7.37(1H, s), 6.03(1H, m),4.87(1H, m), 4.63(2H, q), 2.84(1H, m) 2.45(1H, m), 1.08(3H, t) 7-38.87(1H, d), 8.62(1H, d), 8.33(1H, s), 8.18(1H, d), 8.03(1H, d),7.39(1H, s), 4.93(2H, q), 4.64(2H, q), 3.03(2H, q), 1.20(3H, t) 7-48.85(1H, s), 8.81(1H, d), 8.70(1H, d), 7.84(1H, s), 7.83(1H, s),7.81(1H, d), 7.74(1H, d), 7.68(1H, d), 7.03(1H, s), 2.93(2H, q) 1.36(9H,s), 1.31(3H, t) 7-7 9.17(1H, d), 8.85(1H, s), 8.84(1H, s), 8.64(1H, d),7.94(1H, s), 7.90 (1H, d), 7.80(1H, d), 7.73(1H, d), 7.02(1H, s),3.10(2H, q) 1.37(9H, s), 1.25(3H, t) 7-8 8.90(1H, d), 8.66(1H, d),8.61(1H, d), 7.87(1H, d), 7.19(1H, s), 3.78(2H, q), 2.97(2H, q),1.41(3H, t), 1.33(3H, t) 7-10 8.83(1H, d), 8.80(1H, d), 7.66 (1H, d),7.37(1H, d), 7.00(1H, s), 2.86(2H, q), 1.36(2H, q), 1.24(3H, t) 7-118.85(1H, d), 8.83(1H, d), 8.39(1H, d), 7.67(1H, d), 7.02(1H, s),3.05(2H, q), 1.37(9H, s), 1.22(3H, t) 9-2 9.17(1H, d), 8.61(1H, d),8.52(1H, s), 8.49(1H, d), 7.93(1H, s), 7.89 (1H, d), 7.81(1H, d),7.73(1H, d), 7.20(1H, s), 3.11(2H, q) 1.34(9H, s), 1.28(3H, t) 9-39.13(1H, d), 8.76(1H, d), 8.54(1H, s), 8.13(1H, d), 7.50(1H, s) 3.78(2H,q), 3.09(2H, q), 1.47(3H, t), 1.27(3H, t) 9-4 8.50(1H, d), 8.46(1H, d),8.37(1H, d), 7.70(1H, d), 7.19(1H, s) 3.08(2H, q), 1.34(9H, s), 1.25(3H,t)

The agricultural and horticultural insecticide comprising the1H-pyrrolo-condensed heterocyclic compound represented by the generalformula (1) of the present invention, an N-oxide thereof or a saltthereof as an active ingredient is suitable for controlling a variety ofpests which may damage paddy rice, fruit trees, vegetables, other cropsand ornamental flowering plants. The target pests are, for example,agricultural and forest pests, horticultural pests, stored grain pests,sanitary pests, nematodes, etc.

Specific examples of the pests, nematodes, etc. include the following:

the species of the order Lepidoptera such as Parasa consocia, Anomismesogona, Papilio xuthus, Matsumuraeses azukivora, Ostrinia scapulalis,Spodoptera exempta, Hyphantria cunea, Ostrinia furnacalis, Pseudaletiaseparata, Tinea translucens, Bactra furfurana, Parnara guttata, Marasmiaexigua, Parnara guttata, Sesamia inferens, Brachmia triannulella, Monemaflavescens, Trichoplusia ni, Pleuroptya ruralis, Cystidia couaggaria,Lampides boeticus, Cephonodes hylas, Helicoverpa armigera, Phalerodontamanleyi, Eumeta japonica, Pieris brassicae, Malacosoma neustriatestacea, Stathmopoda masinissa, Cuphodes diospyrosella, Archipsxylosteanus, Agrotis segetum, Tetramoera schistaceana, Papilio machaonhippocrates, Endoclyta sinensis, Lyonetia prunifoliella, Phyllonorycterringoneella, Cydia kurokoi, Eucoenogenes aestuosa, Lobesia botrana,Latoia sinica, Euzophera batangensis, Phalonidia mesotypa, Spilosomaimparilis, Glyphodes pyloalis, Olethreutes mori, Tineola bisselliella,Endoclyta excrescens, Nemapogon granellus, Synanthedon hector, Cydiapomonella, Plutella xylostella, Cnaphalocrocis medinalis,Sesamia calamistis, Scirpophaga incertulas, Pediasia teterrellus,Phthorimaea operculella, Stauropus fagi persimilis, Etiella zinckenella,Spodoptera exigua, Palpifer sexnotata, Spodoptera mauritia, Scirpophagainnotata, Xestia c-nigrum, Spodoptera depravata, Ephestia kuehniella,Angerona prunaria, Clostera anastomosis, Pseudoplusia includens,Matsumuraeses falcana, Helicoverpa assulta, Autographa nigrisigna,Agrotis ipsilon, Euproctis pseudoconspersa, Adoxophyes orana, Caloptiliatheivora, Homona magnanima, Ephestia elutella, Eumeta minuscula,Clostera anachoreta, Heliothis maritima, Sparganothis pilleriana,Busseola fusca, Euproctis subflava, Biston robustum, Heliothis zea,Aedia leucomelas, Narosoideus flavidorsalis, Viminia rumicis,Bucculatrix pyrivorella, Grapholita molesta, Spulerina astaurota,Ectomyelois pyrivorella, Chilo suppressalis, Acrolepiopsis sapporensis,Plodia interpunctella, Hellula undalis, Sitotroga cerealella, Spodopteralitura, a species of the family Tortricidae (Eucosma aporema), Acleriscomariana, Scopelodes contractus, Orgyia thyellina, Spodopterafrugiperda, Ostrinia zaguliaevi, Naranga aenescens, Andraca bipunctata,Paranthrene regalis, Acosmeryx castanea, Phyllocnistis toparcha,Endopiza viteana, Eupoecillia ambiguella, Anticarsia gemmatalis,Cnephasia cinereipalpana,Lymantria dispar, Dendrolimus spectabilis, Leguminivora glycinivorella,Maruca testulalis, Matsumuraeses phaseoli, Caloptilia soyella,Phyllocnistis citrella, Omiodes indicata, Archips fuscocupreanus,Acanthoplusia agnata, Bambalina sp., Carposina niponensis, Conogethespunctiferalis, Synanthedon sp., Lyonetia clerkella, Papilio helenus,Colias erate poliographus, Phalera flavescens, the species of the familyPieridae such as Pieris rapae crucivora and Pieris rapae, Euproctissimilis, Acrolepiopsis suzukiella, Ostrinia nubilalis, Mamestrabrassicae, Ascotis selenaria, Phtheochroides clandestina, Hoshinoaadumbratana, Odonestis pruni japonensis, Triaena intermedia, Adoxophyesorana fasciata, Grapholita inopinata, Spilonota ocellana, Spilonotalechriaspis, Illiberis pruni, Argyresthia conjugella, Caloptiliazachrysa, Archips breviplicanus, Anomis flava, Pectinophora gossypiella,Notarcha derogata, Diaphania indica, Heliothis virescens and Eariascupreoviridis;the species of the order Hemiptera such as Nezara antennata, Stenotusrubrovittatus, Graphosoma rubrolineatum, Trigonotylus coelestialium,Aeschynteles maculatus, Creontiades pallidifer, Dysdercus cingulatus,Chrysomphalus ficus, Aonidiella aurantii, Graptopsaltria nigrofuscata,Blissus leucopterus, Icerya purchasi, Piezodorus hybneri, Lagynotomuselongatus, Thaia subrufa, Scotinophara lurida, Sitobion ibarae,Stariodes iwasakii, Aspidiotus destructor, Taylorilygus pallidulus,Myzus mumecola, Pseudaulacaspis prunicola, Acyrthosiphon pisum,Anacanthocoris striicornis, Ectometopterus micantulus, Eysarcorislewisi, Molipteryx fuliginosa, Cicadella viridis, Rhopalosophumrufiabdominalis, Saissetia oleae, Trialeurodes vaporariorum,Aguriahana quercus, Lygus spp., Euceraphis punctipennis, Andaspiskashicola, Coccus pseudomagnoliarum, Cavelerius saccharivorus, Galeatusspinifrons, Macrosiphoniella sanborni, Aonidiella citrina, Halyomorphamista, Stephanitis fasciicarina, Trioza camphorae, Leptocorisachinensis, Trioza quercicola, Uhlerites latius, Erythroneura comes,Paromius exiguus, Duplaspidiotus claviger, Nephotettix nigropictus,Halticiellus insularis, Perkinsiella saccharicida, Psylla malivorella,Anomomeura mori, Pseudococcus longispinis, Pseudaulacaspis pentagona,Pulvinaria kuwacola, Apolygus lucorum, Togo hemipterus, Toxopteraaurantii, Saccharicoccus sacchari, Geoica lucifuga, Numata muiri,Comstockaspis perniciosa, Unaspis citri, Aulacorthum solani, Eysarcorisventralis, Bemisia argentifolii, Cicadella spectra, Aspidiotus hederae,Liorhyssus hyalinus, Calophya nigridorsalis, Sogatella furcifera,Megoura crassicauda,Brevicoryne brassicae, Aphis glycines, Leptocorisa oratorius,Nephotettix virescens, Uroeucon formosanum, Cyrtopeltis tennuis, Bemisiatabaci, Lecanium persicae, Parlatoria theae, Pseudaonidia paeoniae,Empoasca onukii, Plautia stali, Dysaphis tulipae, Macrosiphumeuphorbiae, Stephanitis pyrioides, Ceroplastes ceriferus, Parlatoriacamelliae, Apolygus spinolai, Nephotettix cincticeps, Glauciassubpunctatus, Orthotylus flavosparsus, Rhopalosiphum maidis, Peregrinusmaidis, Eysarcoris parvus, Cimex lectularius, Psylla abieti, Nilaparvatalugens, Psylla tobirae,Eurydema rugosum, Schizaphis piricola, Psylla pyricola, Parlatoreopsispyri, Stephanitis nashi, Dysmicoccus wistariae, Lepholeucaspis japonica,Sappaphis piri, Lipaphis erysimi, Neotoxoptera formosana, Rhopalosophumnymphaeae, Edwardsiana rosae, Pinnaspis aspidistrae, Psylla alni,Speusotettix subfusculus, Alnetoidia alneti, Sogatella panicicola,Adelphocoris lineolatus, Dysdercus poecilus, Parlatoria ziziphi,Uhlerites debile, Laodelphax striatellus, Eurydema pulchrum, Cletustrigonus, Clovia punctata, Empoasca spp., Coccus hesperidum,Pachybrachius luridus, Planococcus kraunhiae, Stenotus binotatus,Arboridia apicalis, Macrosteles fascifrons, Dolycoris baccarum,Adelphocoris triannulatus, Viteus vitifolii, Acanthocoris sordidus,Leptocorisa acuta, Macropes obnubilus, Cletus punctiger, Riptortusclavatus, Paratrioza cockerelli,Aphrophora costalis, Lygus disponsi, Lygus saundersi, Crisicoccus pini,Empoasca abietis, Crisicoccus matsumotoi, Aphis craccivora, Megacoptapunctatissimum, Eysarcoris guttiger, Lepidosaphes beckii, Diaphorinacitri, Toxoptera citricidus, Planococcus citri, Dialeurodes citri,Aleurocanthus spiniferus, Pseudococcus citriculus, Zyginella citri,Pulvinaria citricola, Coccus discrepans, Pseudaonidia duplex, Pulvinariaaurantii, Lecanium corni, Nezara viridula, Stenodema calcaratum,Rhopalosiphum padi, Sitobion akebiae, Schizaphis graminum, Sorhoanustritici, Brachycaudus helichrysi, Carpocoris purpureipennis, Myzuspersicae, Hyalopterus pruni, Aphis farinose yanagicola, Metasalispopuli, Unaspis yanonensis, Mesohomotoma camphorae, Aphis spiraecola,Aphis pomi, Lepidosaphes ulmi, Psylla mali, Heterocordylus flavipes,Myzus malisuctus, Aphidonuguis mali, Orientus ishidai, Ovatusmalicolens, Eriosoma lanigerum, Ceroplastes rubens and Aphis gossypii;the species of the order Coleoptera such as Xystrocera globosa, Paederusfuscipes, Eucetonia roelofsi, Callosobruchus chinensis, Cylasformicarius, Hypera postica, Echinocnemus squameus, Oulema oryzae,Donacia provosti, Lissorhoptrus oryzophilus, Colasposoma dauricum,Euscepes postfasciatus, Epilachna varivestis, Acanthoscelides obtectus,Diabrotica virgifera virgifera, Involvulus cupreus, Aulacophorafemoralis, Bruchus pisorum, Epilachna vigintioctomaculata, Carpophilusdimidiatus, Cassida nebulosa, Luperomorpha tunebrosa, Phyllotretastriolata, Psacothea hilaris, Aeolesthes chrysothrix, Curculiosikkimensis, Carpophilus hemipterus, Oxycetonia jucunda, Diabroticaspp., Mimela splendens, Sitophilus zeamais, Tribolium castaneum,Sitophilus oryzae, Palorus subdepressus, Melolontha japonica,Anoplophora malasiaca, Neatus picipes, Leptinotarsa decemlineata,Diabrotica undecimpunctata howardi, Sphenophorus venatus, Criocerisquatuordecimpunctata, Conotrachelus nenuphar, Ceuthorhynchidiusalbosuturalis, Phaedon brassicae, Lasioderma serricorne, Sitonajaponicus, Adoretus tenuimaculatus, Tenebrio molitor, Basilepta balyi,Hypera nigrirostris, Chaetocnema concinna, Anomala cuprea, Heptophyllapicea, Epilachna vigintioctopunctata, Diabrotica longicornis, Eucetoniapilifera, Agriotes spp., Attagenus unicolor japonicus, Pagria signata,Anomala rufocuprea, Palorus ratzeburgii, Alphitobius laevigatus,Anthrenus verbasci, Lyctus brunneus, Tribolium confusum, Medythianigrobilineata, Xylotrechus pyrrhoderus, Epitrix cucumeris, Tomicuspiniperda, Monochamus alternatus, Popillia japonica, Epicauta gorhami,Sitophilus zeamais, Rhynchites heros, Listroderes costirostris,Callosobruchus maculatus, Phyllobius armatus, Anthonomus pomorum,Linaeidea aenea and Anthonomus grandis;the species of the order Diptera such as Culex pipiens pallens, Pegomyahyoscyami, Liriomyza huidobrensis, Musca domestica, Chlorops oryzae,Hydrellia sasakii, Agromyza oryzae, Hydrellia griseola, Hydrelliagriseola, Ophiomyia phaseoli, Dacus cucurbitae, Drosophila suzukii,Rhacochlaena japonica, Muscina stabulans, the species of the familyPhoridae such as Megaselia spiracularis, Clogmia albipunctata, Tipulaaino, Phormia regina, Culex tritaeniorhynchus, Anopheles sinensis,Hylemya brassicae, Asphondylia sp., Delia platura, Delia antiqua,Rhagoletis cerasi, Culex pipiens molestus Forskal, Ceratitis capitata,Bradysia agrestis, Pegomya cunicularia, Liriomyza sativae, Liriomyzabryoniae, Chromatomyia horticola, Liriomyza chinensis, Culexquinquefasciatus, Aedes aegypti, Aedes albopictus, Liriomyza trifolii,Liriomyza sativae, Dacus dorsalis, Dacus tsuneonis, Sitodiplosismosellana, Meromuza nigriventris, Anastrepha ludens and Rhagoletispomonella;the species of the order Hymenoptera such as Pristomyrmex pungens, thespecies of the family Bethylidae, Monomorium pharaonis, Pheidole noda,Athalia rosae, Dryocosmus kuriphilus, Formica fusca japonica, thespecies of the subfamily Vespinae, Athalia infumata infumata, Argepagana, Athalia japonica, Acromyrmex spp., Solenopsis spp., Arge maliand Ochetellus glaber;the species of the order Orthoptera such as Homorocoryphus lineosus,Gryllotalpa sp., Oxya hyla intricata, Oxya yezoensis, Locustamigratoria, Oxya japonica, Homorocoryphus jezoensis and Teleogryllusemma;the species of the order Thysanoptera such as Selenothrips rubrocinctus,Stenchaetothrips biformis, Haplothrips aculeatus, Ponticulothripsdiospyrosi, Thrips flavus, Anaphothrips obscurus, Liothrips floridensis,Thrips simplex, Thrips nigropilosus, Heliothrips haemorrhoidalis,Pseudodendrothrips mori, Microcephalothrips abdominalis, Leeuweniapasanii, Litotetothrips pasaniae, Scirtothrips citri, Haplothripschinensis, Mycterothrips glycines, Thrips setosus, Scirtothripsdorsalis, Dendrothrips minowai, Haplothrips niger, Thrips tabaci, Thripsalliorum, Thrips hawaiiensis, Haplothrips kurdjumovi, Chirothripsmanicatus, Frankliniella intonsa, Thrips coloratus, Franklinellaoccidentalis, Thrips palmi, Frankliniella lilivora and Liothripsvaneeckei;the species of the order Acari such as Leptotrombidium akamushi,Tetranychus ludeni, Dermacentor variabilis, Tetranychus truncatus,Ornithonyssus bacoti, Demodex canis, Tetranychus viennensis, Tetranychuskanzawai, the species of the family Ixodidae such as Rhipicephalussanguineus, Cheyletus malaccensis, Tyrophagus putrescentiae,Dermatophagoides farinae, Latrodectus hasseltii, Dermacentor taiwanicus,Acaphylla theavagrans, Polyphagotarsonemus latus, Aculops lycopersici,Ornithonyssus sylvairum, Tetranychus urticae, Eriophyes chibaensis,Sarcoptes scabiei, Haemaphysalis longicornis, Ixodes scapularis,Tyrophagus similis, Cheyletus eruditus, Panonychus citri, Cheyletusmoorei, Brevipalpus phoenicis, Octodectes cynotis, Dermatophagoidesptrenyssnus, Haemaphysalis flava, Ixodes ovatus, Phyllocoptruta citri,Aculus schlechtendali, Panonychus ulmi, Amblyomma americanum,Dermanyssus gallinae, Rhyzoglyphus robini and Sancassania sp.;the species of the order Isoptera such as Reticulitermes miyatakei,Incisitermes minor, Coptotermes formosanus, Hodotermopsis japonica,Reticulitermes sp., Reticulitermes flaviceps amamianus, Glyptotermeskushimensis, Coptotermes guangzhoensis, Neotermes koshunensis,Glyptotermes kodamai, Glyptotermes satsumensis, Cryptotermes domesticus,Odontotermes formosanus, Glyptotermes nakajimai, Pericapritermes nitobeiand Reticulitermes speratus;the species of the order Blattodea such as Periplaneta fuliginosa,Blattella germanica, Blatta orientalis, Periplaneta brunnea, Blattellalituricollis, Periplaneta japonica and Periplaneta americana;the species of the order Siphonaptera such as Pulex irritans,Ctenocephalides felis and Ceratophyllus gallinae;the species of the phylum Nematoda such as Nothotylenchus acris,Aphelenchoides besseyi, Pratylenchus penetrans, Meloidogyne hapla,Meloidogyne incognita, Globodera rostochiensis, Meloidogyne javanica,Heterodera glycines, Pratylenchus coffeae, Pratylenchus neglectus andTylenchus semipenetrans; andthe species of the phylum Mollusca such as Pomacea canaliculata,Achatina fulica, Meghimatium bilineatum, Lehmannina valentiana, Limaxflavus and Acusta despecta sieboldiana.

In addition, the agricultural and horticultural insecticide of thepresent invention has a strong insecticidal effect on Tuta absoluta aswell.

Further, mites and ticks parasitic on animals are also included in thetarget pests, and the examples include the species of the familyIxodidae such as Boophilus microplus, Rhipicephalus sanguineus,Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysaliscampanulata, Haemaphysalis concinna, Haemaphysalis japonica,Haemaphysalis kitaokai, Haemaphysalis ias, Ixodes ovatus, Ixodesnipponensis, Ixodes persulcatus, Amblyomma testudinarium, Haemaphysalismegaspinosa, Dermacentor reticulatus and Dermacentor taiwanesis;Dermanyssus gallinae; the species of the genus Ornithonyssus such asOrnithonyssus sylviarum and Ornithonyssus bursa; the species of thefamily Trombiculidae such as Eutrombicula wichmanni, Leptotrombidiumakamushi, Leptotrombidium pallidum, Leptotrombidium fuji,Leptotrombidium tosa, Neotrombicula autumnalis, Eutrombiculaalfreddugesi and Helenicula miyagawai; the species of the familyCheyletidae such as Cheyletiella yasguri, Cheyletiella parasitivorax andCheyletiella blakei; the species of the superfamily Sarcoptoidea such asPsoroptes cuniculi, Chorioptes bovis, Otodectes cynotis, Sarcoptesscabiei and Notoedres cati; and the species of the family Demodicidaesuch as Demodex canis.

Other target pests include fleas including ectoparasitic winglessinsects belonging to the order Siphonaptera, more specifically, thespecies belonging to the families Pulicidae and Ceratophyllidae.Examples of the species belonging to the family Pulicidae includeCtenocephalides canis, Ctenocephalides felis, Pulex irritans,Echidnophaga gallinacea, Xenopsylla cheopis, Leptopsylla segnis,Nosopsyllus fasciatus and Monopsyllus anisus.

Other target pests include ectoparasites, for example, the species ofthe suborder Anoplura such as Haematopinus eurysternus, Haematopinusasini, Dalmalinia ovis, Linognathus vituli, Haematopinus suis, Phthiruspubis and Pediculus capitis; the species of the suborder Mallophaga suchas Trichodectes canis; and hematophagous Dipteran insect pests such asTabanus trigonus, Culicoides schultzei and Simulium ornatum. Inaddition, examples of endoparasites include nematodes such as lungworms,whipworms, nodular worms, endogastric parasitic worms, ascarides andfilarial worms; cestodes such as Spirometra erinacei, Diphyllobothriumlatum, Dipylidium caninum, Multiceps multiceps, Echinococcus granulosusand Echinococcus multilocularis; trematodes such as Schistosomajaponicum and Fasciola hepatica; and protozoa such as coccidia,Plasmodium, intestinal Sarcocystis, Toxoplasma and Cryptosporidium.

The agricultural and horticultural insecticide comprising the1H-pyrrolo-condensed heterocyclic compound represented by the generalformula (1) of the present invention, an N-oxide thereof or a saltthereof as an active ingredient has a remarkable control effect on theabove-described pests which damage lowland crops, field crops, fruittrees, vegetables, other crops, ornamental flowering plants, etc. Thedesired effect can be obtained when the agricultural and horticulturalinsecticide is applied to nursery facilities for seedlings, paddyfields, fields, fruit trees, vegetables, other crops, ornamentalflowering plants, etc. and their seeds, paddy water, foliage,cultivation media such as soil, or the like around the expected time ofpest infestation, i.e., before the infestation or upon the confirmationof the infestation. In particularly preferable embodiments, theapplication of the agricultural and horticultural insecticide utilizesso-called penetration and translocation. That is, nursery soil, soil intransplanting holes, plant foot, irrigation water, cultivation water inhydroponics, or the like is treated with the agricultural andhorticultural insecticide to allow crops, ornamental flowering plants,etc. to absorb the compound of the present invention through the rootsvia soil or otherwise.

Examples of useful plants to which the agricultural and horticulturalinsecticide of the present invention can be applied include, but are notparticularly limited to, cereals (e.g., rice, barley, wheat, rye, oats,corn, etc.), legumes (e.g., soybeans, azuki beans, broad beans, greenpeas, kidney beans, peanuts, etc.), fruit trees and fruits (e.g.,apples, citrus fruits, pears, grapes, peaches, plums, cherries, walnuts,chestnuts, almonds, bananas, etc.), leaf and fruit vegetables (e.g.,cabbages, tomatoes, spinach, broccoli, lettuce, onions, green onions(chives and Welsh onions), green peppers, eggplants, strawberries,pepper crops, okra, Chinese chives, etc.), root vegetables (e.g.,carrots, potatoes, sweet potatoes, taros, Japanese radishes, turnips,lotus roots, burdock roots, garlic, Chinese scallions, etc.), crops forprocessing (e.g., cotton, hemp, beet, hops, sugarcane, sugar beet,olives, rubber, coffee, tobacco, tea, etc.), gourds (e.g., Japanesepumpkins, cucumbers, watermelons, oriental sweet melons, melons, etc.),pasture grass (e.g., orchardgrass, sorghum, timothy, clover, alfalfa,etc.), lawn grass (e.g., Korean lawn grass, bent grass, etc.), spice andaromatic crops and ornamental crops (e.g., lavender, rosemary, thyme,parsley, pepper, ginger, etc.), ornamental flowering plants (e.g.,chrysanthemum, rose, carnation, orchid, tulip, lily, etc.), garden trees(e.g., ginkgo trees, cherry trees, Japanese aucuba, etc.) and foresttrees (e.g., Abies sachalinensis, Picea jezoensis, pine, yellow cedar,Japanese cedar, hinoki cypress, eucalyptus, etc.).

The above-mentioned “plants” also include plants provided with herbicidetolerance by a classical breeding technique or a gene recombinationtechnique. Examples of such herbicide tolerance include tolerance toHPPD inhibitors, such as isoxaflutole; ALS inhibitors, such asimazethapyr and thifensulfuron-methyl; EPSP synthase inhibitors, such asglyphosate; glutamine synthetase inhibitors, such as glufosinate;acetyl-CoA carboxylase inhibitors, such as sethoxydim; or otherherbicides, such as bromoxynil, dicamba and 2,4-D.

Examples of the plants provided with herbicide tolerance by a classicalbreeding technique include varieties of rapeseed, wheat, sunflower andrice tolerant to the imidazolinone family of ALS-inhibiting herbicidessuch as imazethapyr, and such plants are sold under the trade name ofClearfield (registered trademark). Also included is a variety of soybeanprovided with tolerance to the sulfonyl urea family of ALS-inhibitingherbicides such as thifensulfuron-methyl by a classical breedingtechnique, and this is sold under the trade name of STS soybean. Alsoincluded are plants provided with tolerance to acetyl-CoA carboxylaseinhibitors such as trione oxime herbicides and aryloxy phenoxy propionicacid herbicides by a classical breeding technique, for example, SR cornand the like.

Plants provided with tolerance to acetyl-CoA carboxylase inhibitors aredescribed in Proc. Natl. Acad. Sci. USA, 87, 7175-7179 (1990), and thelike. Further, acetyl-CoA carboxylase mutants resistant to acetyl-CoAcarboxylase inhibitors are reported in Weed Science, 53, 728-746 (2005),and the like, and by introducing the gene of such an acetyl-CoAcarboxylase mutant into plants by a gene recombination technique, orintroducing a resistance-conferring mutation into acetyl-CoA carboxylaseof plants, plants tolerant to acetyl-CoA carboxylase inhibitors can beengineered. Alternatively, by introducing a nucleic acid causing basesubstitution mutation into plant cells (a typical example of thistechnique is chimeraplasty technique (Gura T. 1999. Repairing theGenome's Spelling Mistakes. Science 285: 316-318.)) to allowsite-specific substitution mutation in the amino acids encoded by anacetyl-CoA carboxylase gene, an ALS gene or the like of plants, plantstolerant to acetyl-CoA carboxylase inhibitors, ALS inhibitors or thelike can be engineered. The agricultural and horticultural insecticideof the present invention can be applied to these plants as well.

Further, exemplary toxins expressed in genetically modified plantsinclude insecticidal proteins of Bacillus cereus or Bacillus popilliae;Bacillus thuringiensis 6-endotoxins, such as Cry1Ab, Cry1Ac, Cry1F,Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 and Cry9C, and other insecticidalproteins, such as VIP1, VIP2, VIP3 and VIP3A; nematode insecticidalproteins; toxins produced by animals, such as scorpion toxins, spidertoxins, bee toxins and insect-specific neurotoxins; toxins offilamentous fungi; plant lectins; agglutinin; protease inhibitors, suchas trypsin inhibitors, serine protease inhibitors, patatin, cystatin andpapain inhibitors; ribosome inactivating proteins (RIP), such as ricin,maize RIP, abrin, luffin, saporin and bryodin; steroid metabolizingenzymes, such as 3-hydroxy steroid oxidase,ecdysteroid-UDP-glucosyltransferase and cholesterol oxidase; ecdysoneinhibitors; HMG-CoA reductase; ion channel inhibitors, such as sodiumchannel inhibitors and calcium channel inhibitors; juvenile hormoneesterase; diuretic hormone receptors; stilbene synthase; bibenzylsynthase; chitinase; and glucanase.

Also included are hybrid toxins, partially deficient toxins and modifiedtoxins derived from the following: δ-endotoxin proteins such as Cry1Ab,Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab andCry35Ab, and other insecticidal proteins such as VIP1, VIP2, VIP3 andVIP3A. The hybrid toxin can be produced by combining some domains ofthese proteins differently from the original combination in nature withthe use of a recombination technique. As the partially deficient toxin,a Cry1Ab toxin in which a part of the amino acid sequence is deleted isknown. In the modified toxin, one or more amino acids of a naturallyoccurring toxin are substituted.

Examples of the foregoing toxins and genetically modified plants capableof synthesizing these toxins are described in EP-A-0 374 753, WO93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878, WO 03/052073, etc.

Due to the toxins contained in such genetically modified plants, theplants exhibit resistance to pests, in particular, Coleopteran insectpests, Hemipteran insect pests, Dipteran insect pests, Lepidopteraninsect pests and nematodes. The above-described technologies and theagricultural and horticultural insecticide of the present invention canbe used in combination or used systematically.

In order to control target pests, the agricultural and horticulturalinsecticide of the present invention, with or without appropriatedilution or suspension in water etc., is applied to plants potentiallyinfested with the target insect pests or nematodes in an amounteffective for the control of the insect pests or nematodes. For example,in order to control insect pests and nematodes that may damage cropplants such as fruit trees, cereals and vegetables, foliar applicationand seed treatment such as dipping, dust coating and calcium peroxidecoating can be performed. Further, treatment of or application to soilor the like may also be performed to allow plants to absorbagrochemicals through their roots. Examples of such treatment includewhole soil incorporation, planting row treatment, bed soilincorporation, plug seedling treatment, planting hole treatment, plantfoot treatment, top-dressing, treatment of nursery boxes for paddy rice,and submerged application. In addition, application to culture media inhydroponics, smoking treatment, trunk injection and the like can also beperformed.

Further, the agricultural and horticultural insecticide of the presentinvention, with or without appropriate dilution or suspension in wateretc., can be applied to sites potentially infested with pests in anamount effective for the control of the pests. For example, it can bedirectly applied to stored grain pests, house pests, sanitary pests,forest pests, etc., and also be used for coating of residential buildingmaterials, for smoking treatment, or as a bait formulation.

Exemplary methods of seed treatment include dipping of seeds in adiluted or undiluted fluid of a liquid or solid formulation for thepermeation of agrochemicals into the seeds; mixing or dust coating ofseeds with a solid or liquid formulation for the adherence of theformulation onto the surfaces of the seeds; coating of seeds with amixture of a solid or liquid formulation and an adhesive carrier such asresins and polymers; and application of a solid or liquid formulation tothe vicinity of seeds at the same time as seeding.

The term “seed” in the above-mentioned seed treatment refers to a plantbody which is in the early stages of cultivation and used for plantpropagation. The examples include, in addition to a so-called seed, aplant body for vegetative propagation, such as a bulb, a tuber, a seedpotato, a bulbil, a propagule, a discoid stem and a stem used forcuttage.

The term “soil” or “cultivation medium” in the method of the presentinvention for using an agricultural and horticultural insecticide refersto a support medium for crop cultivation, in particular a support mediumwhich allows crop plants to spread their roots therein, and thematerials are not particularly limited as long as they allow plants togrow. Examples of the support medium include what is called soils,seedling mats and water, and specific examples of the materials includesand, pumice, vermiculite, diatomite, agar, gelatinous substances,high-molecular-weight substances, rock wool, glass wool, wood chip andbark.

Exemplary methods of the application to crop foliage or to stored grainpests, house pests, sanitary pests, forest pests, etc. includeapplication of a liquid formulation, such as an emulsifiable concentrateand a flowable, or a solid formulation, such as a wettable powder and awater-dispersible granule, after appropriate dilution in water; dustapplication; and smoking.

Exemplary methods of soil application include application of awater-diluted or undiluted liquid formulation to the foot of plants,nursery beds for seedlings, or the like; application of a granule to thefoot of plants, nursery beds for seedlings, or the like; application ofa dust, a wettable powder, a water-dispersible granule, a granule or thelike onto soil and subsequent incorporation of the formulation into thewhole soil before seeding or transplanting; and application of a dust, awettable powder, a water-dispersible granule, a granule or the like toplanting holes, planting rows or the like before seeding or planting.

To nursery boxes for paddy rice, for example, a dust, awater-dispersible granule, a granule or the like can be applied,although the suitable formulation may vary depending on the applicationtiming, in other words, depending on the cultivation stage such asseeding time, greening period and planting time. A formulation such as adust, a water-dispersible granule and a granule may be mixed withnursery soil. For example, such a formulation is incorporated into bedsoil, covering soil or the whole soil. Simply, nursery soil and such aformulation may be alternately layered.

In the application to paddy fields, a solid formulation, such as ajumbo, a pack, a granule and a water-dispersible granule, or a liquidformulation, such as a flowable and an emulsifiable concentrate, isapplied usually to flooded paddy fields. In a rice planting period, asuitable formulation, as it is or after mixed with a fertilizer, may beapplied onto soil or injected into soil. In addition, an emulsifiableconcentrate, a flowable or the like may be applied to the source ofwater supply for paddy fields, such as a water inlet and an irrigationdevice. In this case, treatment can be accomplished with the supply ofwater and thus achieved in a labor-saving manner.

In the case of field crops, their seeds, cultivation media in thevicinity of their plants, or the like may be treated in the period ofseeding to seedling culture. In the case of plants of which the seedsare directly sown in the field, in addition to direct seed treatment,plant foot treatment during cultivation is preferable. Specifically, thetreatment can be performed by, for example, applying a granule ontosoil, or drenching soil with a formulation in a water-diluted orundiluted liquid form. Another preferable treatment is incorporation ofa granule into cultivation media before seeding.

In the case of culture plants to be transplanted, preferable examples ofthe treatment in the period of seeding to seedling culture include, inaddition to direct seed treatment, drench treatment of nursery beds forseedlings with a formulation in a liquid form; and granule applicationto nursery beds for seedlings. Also included are treatment of plantingholes with a granule; and incorporation of a granule into cultivationmedia in the vicinity of planting points at the time of fix planting.

The agricultural and horticultural insecticide of the present inventionis commonly used as a formulation convenient for application, which isprepared in the usual method for preparing agrochemical formulations.

That is, the condensed heterocyclic compound represented by the generalformula (1) of the present invention, an N-oxide thereof or a saltthereof and an appropriate inactive carrier, and if needed an adjuvant,are blended in an appropriate ratio, and through the step ofdissolution, separation, suspension, mixing, impregnation, adsorptionand/or adhesion, are formulated into an appropriate form forapplication, such as a suspension concentrate, an emulsifiableconcentrate, a soluble concentrate, a wettable powder, awater-dispersible granule, a granule, a dust, a tablet and a pack.

The composition (agricultural and horticultural insecticide or animalparasite control agent) of the present invention can optionally containan additive usually used for agrochemical formulations or animalparasite control agents in addition to the active ingredient. Examplesof the additive include carriers such as solid or liquid carriers,surfactants, dispersants, wetting agents, binders, tackifiers,thickeners, colorants, spreaders, sticking/spreading agents,antifreezing agents, anti-caking agents, disintegrants and stabilizingagents. If needed, preservatives, plant fragments, etc. may also be usedas the additive. One of these additives may be used alone, and also twoor more of them may be used in combination.

Examples of the solid carriers include natural minerals, such as quartz,clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay,attapulgite, zeolite and diatomite; inorganic salts, such as calciumcarbonate, ammonium sulfate, sodium sulfate and potassium chloride;organic solid carriers, such as synthetic silicic acid, syntheticsilicates, starch, cellulose and plant powders (for example, sawdust,coconut shell, corn cob, tobacco stalk, etc.); plastics carriers, suchas polyethylene, polypropylene and polyvinylidene chloride; urea; hollowinorganic materials; hollow plastic materials; and fumed silica (whitecarbon). One of these solid carriers may be used alone, and also two ormore of them may be used in combination.

Examples of the liquid carriers include alcohols including monohydricalcohols, such as methanol, ethanol, propanol, isopropanol and butanol,and polyhydric alcohols, such as ethylene glycol, diethylene glycol,propylene glycol, hexylene glycol, polyethylene glycol, polypropyleneglycol and glycerin; polyol compounds, such as propylene glycol ether;ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone,diisobutyl ketone and cyclohexanone; ethers, such as ethyl ether,dioxane, ethylene glycol monoethyl ether, dipropyl ether andtetrahydrofuran; aliphatic hydrocarbons, such as normal paraffin,naphthene, isoparaffin, kerosene and mineral oil; aromatic hydrocarbons,such as benzene, toluene, xylene, solvent naphtha and alkyl naphthalene;halogenated hydrocarbons, such as dichloromethane, chloroform and carbontetrachloride; esters, such as ethyl acetate, diisopropyl phthalate,dibutyl phthalate, dioctyl phthalate and dimethyl adipate; lactones,such as γ-butyrolactone; amides, such as dimethylformamide,diethylformamide, dimethylacetamide and N-alkyl pyrrolidinone; nitriles,such as acetonitrile; sulfur compounds, such as dimethyl sulfoxide;vegetable oils, such as soybean oil, rapeseed oil, cotton seed oil andcastor oil; and water. One of these liquid carriers may be used alone,and also two or more of them may be used in combination.

Exemplary surfactants used as the dispersant or the wetting/spreadingagent include nonionic surfactants, such as sorbitan fatty acid ester,polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester,polyoxyethylene fatty acid ester, polyoxyethylene resin acid ester,polyoxyethylene fatty acid diester, polyoxyethylene alkyl ether,polyoxyethylene alkyl aryl ether, polyoxyethylene alkyl phenyl ether,polyoxyethylene dialkyl phenyl ether, polyoxyethylene alkyl phenylether-formaldehyde condensates, polyoxyethylene-polyoxypropylene blockcopolymers, polystyrene-polyoxyethylene block polymers, alkylpolyoxyethylene-polypropylene block copolymer ether, polyoxyethylenealkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acidbis(phenyl ether), polyalkylene benzyl phenyl ether, polyoxyalkylenestyryl phenyl ether, acetylene diol, polyoxyalkylene-added acetylenediol, polyoxyethylene ether-type silicone, ester-type silicone,fluorosurfactants, polyoxyethylene castor oil and polyoxyethylenehydrogenated castor oil; anionic surfactants, such as alkyl sulfates,polyoxyethylene alkyl ether sulfates, polyoxyethylene alkyl phenyl ethersulfates, polyoxyethylene styryl phenyl ether sulfates, alkylbenzenesulfonates, alkylaryl sulfonates, lignosulfonates, alkylsulfosuccinates, naphthalene sulfonates, alkylnaphthalene sulfonates,salts of naphthalenesulfonic acid-formaldehyde condensates, salts ofalkylnaphthalenesulfonic acid-formaldehyde condensates, fatty acidsalts, polycarboxylic acid salts, polyacrylates, N-methyl-fatty acidsarcosinates, resinates, polyoxyethylene alkyl ether phosphates andpolyoxyethylene alkyl phenyl ether phosphates; cationic surfactantsincluding alkyl amine salts, such as lauryl amine hydrochloride, stearylamine hydrochloride, oleyl amine hydrochloride, stearyl amine acetate,stearyl aminopropyl amine acetate, alkyl trimethyl ammonium chloride andalkyl dimethyl benzalkonium chloride; and amphoteric surfactants, suchas amino acid-type or betaine-type amphoteric surfactants. One of thesesurfactants may be used alone, and also two or more of them may be usedin combination.

Examples of the binders or the tackifiers include carboxymethylcellulose or salts thereof, dextrin, soluble starch, xanthan gum, guargum, sucrose, polyvinyl pyrrolidone, gum arabic, polyvinyl alcohol,polyvinyl acetate, sodium polyacrylate, polyethylene glycols with anaverage molecular weight of 6,000 to 20,000, polyethylene oxides with anaverage molecular weight of 100,000 to 5,000,000, phospholipids (forexample, cephalin, lecithin, etc.), cellulose powder, dextrin, modifiedstarch, polyaminocarboxylic acid chelating compounds, cross-linkedpolyvinyl pyrrolidone, maleic acid-styrene copolymers, (meth)acrylicacid copolymers, half esters of polyhydric alcohol polymer anddicarboxylic anhydride, water soluble polystyrene sulfonates, paraffin,terpene, polyamide resins, polyacrylates, polyoxyethylene, waxes,polyvinyl alkyl ether, alkylphenol-formaldehyde condensates andsynthetic resin emulsions.

Examples of the thickeners include water soluble polymers, such asxanthan gum, guar gum, diutan gum, carboxymethyl cellulose, polyvinylpyrrolidone, carboxyvinyl polymers, acrylic polymers, starch compoundsand polysaccharides; and inorganic fine powders, such as high gradebentonite and fumed silica (white carbon).

Examples of the colorants include inorganic pigments, such as ironoxide, titanium oxide and Prussian blue; and organic dyes, such asalizarin dyes, azo dyes and metal phthalocyanine dyes.

Examples of the antifreezing agents include polyhydric alcohols, such asethylene glycol, diethylene glycol, propylene glycol and glycerin.

Examples of the adjuvants serving to prevent caking or facilitatedisintegration include polysaccharides (starch, alginic acid, mannose,galactose, etc.), polyvinyl pyrrolidone, fumed silica (white carbon),ester gum, petroleum resin, sodium tripolyphosphate, sodiumhexametaphosphate, metal stearates, cellulose powder, dextrin,methacrylate copolymers, polyvinyl pyrrolidone, polyaminocarboxylic acidchelating compounds, sulfonated styrene-isobutylene-maleic anhydridecopolymers and starch-polyacrylonitrile graft copolymers.

Examples of the stabilizing agents include desiccants, such as zeolite,quicklime and magnesium oxide; antioxidants, such as phenolic compounds,amine compounds, sulfur compounds and phosphoric acid compounds; andultraviolet absorbers, such as salicylic acid compounds and benzophenonecompounds.

Examples of the preservatives include potassium sorbate and1,2-benzothiazolin-3-one.

Further, other adjuvants including functional spreading agents, activityenhancers such as metabolic inhibitors (piperonyl butoxide etc.),antifreezing agents (propylene glycol etc.), antioxidants (BHT etc.) andultraviolet absorbers can also be used if needed.

The amount of the active ingredient compound in the agricultural andhorticultural insecticide of the present invention can be adjusted asneeded, and basically, the amount of the active ingredient compound isappropriately selected from the range of 0.01 to 90 parts by weight in100 parts by weight of the agricultural and horticultural insecticide.For example, in the case where the agricultural and horticulturalinsecticide is a dust, a granule, an emulsifiable concentrate or awettable powder, it is suitable that the amount of the active ingredientcompound is 0.01 to 50 parts by weight (0.01 to 50% by weight relativeto the total weight of the agricultural and horticultural insecticide).

The application rate of the agricultural and horticultural insecticideof the present invention may vary with various factors, for example, thepurpose, the target pest, the growing conditions of crops, the tendencyof pest infestation, the weather, the environmental conditions, thedosage form, the application method, the application site, theapplication timing, etc., but basically, the application rate of theactive ingredient compound is appropriately selected from the range of0.001 g to 10 kg, and preferably 0.01 g to 1 kg per 10 ares depending onthe purpose.

Furthermore, for the expansion of the range of target pests and theappropriate time for pest control, or for dose reduction, theagricultural and horticultural insecticide of the present invention canbe used after mixed with other agricultural and horticulturalinsecticides, acaricides, nematicides, microbicides, biopesticidesand/or the like. Further, the agricultural and horticultural insecticidecan be used after mixed with herbicides, plant growth regulators,fertilizers and/or the like depending on the situation.

Examples of such additional agricultural and horticultural insecticides,acaricides and nematicides used for the above-mentioned purposes include3,5-xylyl methylcarbamate (XMC), crystalline protein toxins produced byBacillus thuringiensis such as Bacillus thuringiensis aizawai, Bacillusthuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillusthuringiensis kurstaki and Bacillus thuringiensis tenebrionis, BPMC, Bttoxin-derived insecticidal compounds, CPCBS (chlorfenson), DCIP(dichlorodiisopropyl ether), D-D (1,3-dichloropropene), DDT, NAC,O-4-dimethylsulfamoylphenyl O,O-diethyl phosphorothioate (DSP), O-ethylO-4-nitrophenyl phenylphosphonothioate (EPN), tripropylisocyanurate(TPIC), acrinathrin, azadirachtin, azinphos-methyl, acequinocyl,acetamiprid, acetoprole, acephate, abamectin, avermectin-B, amidoflumet,amitraz, alanycarb, aldicarb, aldoxycarb, aldrin, alpha-endosulfan,alpha-cypermethrin, albendazole, allethrin, isazofos, isamidofos,isoamidofos isoxathion, isofenphos, isoprocarb (MIPC), ivermectin,imicyafos, imidacloprid, imiprothrin, indoxacarb, esfenvalerate,ethiofencarb, ethion, ethiprole, etoxazole, ethofenprox, ethoprophos,etrimfos, emamectin, emamectin-benzoate, endosulfan, empenthrin,

oxamyl, oxydemeton-methyl, oxydeprofos (ESP), oxibendazole, oxfendazole,potassium oleate, sodium oleate, cadusafos, cartap, carbaryl,carbosulfan, carbofuran, gamma-cyhalothrin, xylylcarb, quinalphos,kinoprene, chinomethionat, cloethocarb, clothianidin, clofentezine,chromafenozide, chlorantraniliprole, chlorethoxyfos, chlordimeform,chlordane, chlorpyrifos, chlorpyrifos-methyl, chlorphenapyr,chlorfenson, chlorfenvinphos, chlorfluazuron, chlorobenzilate,chlorobenzoate, kelthane (dicofol), salithion, cyanophos (CYAP),diafenthiuron, diamidafos, cyantraniliprole, theta-cypermethrin,dienochlor, cyenopyrafen, dioxabenzofos, diofenolan, sigma-cypermethrin,dichlofenthion (ECP), cycloprothrin, dichlorvos (DDVP), disulfoton,dinotefuran, cyhalothrin, cyphenothrin, cyfluthrin, diflubenzuron,cyflumetofen, diflovidazin, cyhexatin, cypermethrin, dimethylvinphos,dimethoate, dimefluthrin, silafluofen, cyromazine, spinetoram, spinosad,spirodiclofen, spirotetramat, spiromesifen, sulfluramid, sulprofos,sulfoxaflor, zeta-cypermethrin,diazinon, tau-fluvalinate, dazomet, thiacloprid, thiamethoxam,thiodicarb, thiocyclam, thiosultap, thiosultap-sodium, thionazin,thiometon, deet, dieldrin, tetrachlorvinphos, tetradifon,tetramethylfluthrin, tetramethrin, tebupirimfos, tebufenozide,tebufenpyrad, tefluthrin, teflubenzuron, demeton-S-methyl, temephos,deltamethrin, terbufos, tralopyril, tralomethrin, transfluthrin,triazamate, triazuron, trichlamide, trichlorphon (DEP), triflumuron,tolfenpyrad, naled (BRP), nithiazine, nitenpyram, novaluron,noviflumuron, hydroprene, vaniliprole, vamidothion, parathion,parathion-methyl, halfenprox, halofenozide,bistrifluron, bisultap, hydramethylnon, hydroxy propyl starch,binapacryl, bifenazate, bifenthrin, pymetrozine, pyraclofos,pyrafluprole, pyridafenthion, pyridaben, pyridalyl, pyrifluquinazon,pyriprole, pyriproxyfen, pirimicarb, pyrimidifen, pirimiphos-methyl,pyrethrins, fipronil, fenazaquin, fenamiphos, bromopropylate,fenitrothion (MEP), fenoxycarb, fenothiocarb, phenothrin, fenobucarb,fensulfothion, fenthion (MPP), phenthoate (PAP), fenvalerate,fenpyroximate, fenpropathrin, fenbendazole, fosthiazate, formetanate,butathiofos, buprofezin, furathiocarb, prallethrin, fluacrypyrim,fluazinam, fluazuron, fluensulfone, flucycloxuron, flucythrinate,fluvalinate, flupyrazofos, flufenerim, flufenoxuron, flufenzine,flufenprox, fluproxyfen, flubrocythrinate, flubendiamide, flumethrin,flurimfen, prothiofos, protrifenbute, flonicamid, propaphos, propargite(BPPS), profenofos, profluthrin, propoxur (PHC), bromopropylate,beta-cyfluthrin, hexaflumuron, hexythiazox, heptenophos, permethrin,benclothiaz, bendiocarb, bensultap, benzoximate, benfuracarb, phoxim,phosalone, fosthiazate, fosthietan, phosphamidon, phosphocarb, phosmet(PMP), polynactins, formetanate, formothion, phorate,machine oil, malathion, milbemycin, milbemycin-A, milbemectin, mecarbam,mesulfenfos, methomyl, metaldehyde, metaflumizone, methamidophos,metam-ammonium, metam-sodium, methiocarb, methidathion (DMTP),methylisothiocyanate, methylneodecanamide, methylparathion,metoxadiazone, methoxychlor, methoxyfenozide, metofluthrin, methoprene,metolcarb, meperfluthrin, mevinphos, monocrotophos, monosultap,lambda-cyhalothrin, ryanodine, lufenuron, resmethrin, lepimectin,rotenone, levamisole hydrochloride, fenbutatin oxide, moranteltartarate, methyl bromide, tricyclohexyltin hydroxide (cyhexatin),calcium cyanamide, calcium polysulfide, sulfur and nicotine-sulfate.

Exemplary agricultural and horticultural microbicides used for the samepurposes as above include aureofungin, azaconazole, azithiram,acypetacs, acibenzolar, acibenzolar-S-methyl, azoxystrobin, anilazine,amisulbrom, ampropylfos, ametoctradin, allyl alcohol, aldimorph, amobam,isotianil, isovaledione, isopyrazam, isoprothiolane, ipconazole,iprodione, iprovalicarb, iprobenfos, imazalil, iminoctadine,iminoctadine-albesilate, iminoctadine-triacetate, imibenconazole,uniconazole, uniconazole-P, echlomezole, edifenphos, etaconazole,ethaboxam, ethirimol, etem, ethoxyquin, etridiazole, enestroburin,epoxiconazole, oxadixyl, oxycarboxin, copper-8-quinolinolate,oxytetracycline, copper-oxinate, oxpoconazole, oxpoconazole-fumarate,oxolinic acid, octhilinone, ofurace, orysastrobin,

metam-sodium, kasugamycin, carbamorph, carpropamid, carbendazim,carboxin, carvone, quinazamid, quinacetol, quinoxyfen, quinomethionate,captafol, captan, kiralaxyl, quinconazole, quintozene, guazatine,cufraneb, cuprobam, glyodin, griseofulvin, climbazole, cresol,kresoxim-methyl, chlozolinate, clotrimazole, chlobenthiazone,chloraniformethan, chloranil, chlorquinox, chloropicrin, chlorfenazole,chlorodinitronaphthalene, chlorothalonil, chloroneb, zarilamid,salicylanilide, cyazofamid, diethyl pyrocarbonate, diethofencarb,cyclafuramid, diclocymet, dichlozoline, diclobutrazol, dichlofluanid,cycloheximide, diclomezine, dicloran, dichlorophen, dichlone,disulfiram, ditalimfos, dithianon, diniconazole, diniconazole-M, zineb,dinocap, dinocton, dinosulfon, dinoterbon, dinobuton, dinopenton,dipyrithione, diphenylamine, difenoconazole, cyflufenamid, diflumetorim,cyproconazole, cyprodinil, cyprofuram, cypendazole, simeconazole,dimethirimol, dimethomorph, cymoxanil, dimoxystrobin, methyl bromide,ziram, silthiofam,streptomycin, spiroxamine, sultropen, sedaxane, zoxamide, dazomet,thiadiazin, tiadinil, thiadifluor, thiabendazole, tioxymid,thiochlorfenphim, thiophanate, thiophanate-methyl, thicyofen,thioquinox, chinomethionat, thifluzamide, thiram, decafentin, tecnazene,tecloftalam, tecoram, tetraconazole, debacarb, dehydroacetic acid,tebuconazole, tebufloquin, dodicin, dodine, dodecyl benzensulfonatebis-ethylene diamine copper(II) (DBEDC), dodemorph, drazoxolon,triadimenol, triadimefon, triazbutil, triazoxide, triamiphos, triarimol,trichlamide, tricyclazole, triticonazole, tridemorph, tributyltin oxide,triflumizole, trifloxystrobin, triforine, tolylfluanid,tolclofos-methyl, natamycin, nabam, nitrothal-isopropyl, nitrostyrene,nuarimol, copper nonylphenol sulfonate, halacrinate, validamycin,valifenalate, harpin protein,bixafen, picoxystrobin, picobenzamide, bithionol, bitertanol,hydroxyisoxazole, hydroxyisoxazole-potassium, binapacryl, biphenyl,piperalin, hymexazol, pyraoxystrobin, pyracarbolid, pyraclostrobin,pyrazophos, pyrametostrobin, pyriofenone, pyridinitril, pyrifenox,pyribencarb, pyrimethanil, pyroxychlor, pyroxyfur, pyroquilon,vinclozolin,famoxadone, fenapanil, fenamidone, fenaminosulf, fenarimol, fenitropan,fenoxanil, ferimzone, ferbam, fentin, fenpiclonil, fenpyrazamine,fenbuconazole, fenfuram, fenpropidin, fenpropimorph, fenhexamid,phthalide, buthiobate, butylamine, bupirimate, fuberidazole,blasticidin-S, furametpyr, furalaxyl, fluacrypyrim, fluazinam,fluoxastrobin, fluotrimazole, fluopicolide, fluopyram, fluoroimide,furcarbanil, fluxapyroxad, fluquinconazole, furconazole,furconazole-cis, fludioxonil, flusilazole, flusulfamide, flutianil,flutolanil, flutriafol, furfural, furmecyclox, flumetover, flumorph,proquinazid, prochloraz, procymidone, prothiocarb, prothioconazole,propamocarb, propiconazole, propineb, furophanate, probenazole,bromuconazole,hexachlorobutadiene, hexaconazole, hexylthiofos, bethoxazin, benalaxyl,benalaxyl-M, benodanil, benomyl, pefurazoate, benquinox, penconazole,benzamorf, pencycuron, benzohydroxamic acid, bentaluron, benthiazole,benthiavalicarb-isopropyl, penthiopyrad, penflufen, boscalid,phosdiphen, fosetyl, fosetyl-Al, polyoxins, polyoxorim, polycarbamate,folpet, formaldehyde, machine oil, maneb, mancozeb, mandipropamid,myclozolin, myclobutanil, mildiomycin, milneb, mecarbinzid,methasulfocarb, metazoxolon, metam, metam-sodium, metalaxyl,metalaxyl-M, metiram, methyl isothiocyanate, meptyldinocap, metconazole,metsulfovax, methfuroxam, metominostrobin, metrafenone, mepanipyrim,mefenoxam, meptyldinocap, mepronil, mebenil, iodomethane, rabenzazole,benzalkonium chloride, basic copper chloride, basic copper sulfate,inorganic microbicides such as silver, sodium hypochlorite, cuprichydroxide, wettable sulfur, calcium polysulfide, potassium hydrogencarbonate, sodium hydrogen carbonate, sulfur, copper sulfate anhydride,nickel dimethyldithiocarbamate, copper compounds such ascopper-8-quinolinolate (oxine copper), zinc sulfate and copper sulfatepentahydrate.

Exemplary herbicides used for the same purposes as above include1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4-D,2,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP,MCP, MCPA, MCPA-thioethyl, MCPB, ioxynil, aclonifen, azafenidin,acifluorfen, aziprotryne, azimsulfuron, asulam, acetochlor, atrazine,atraton, anisuron, anilofos, aviglycine, abscisic acid, amicarbazone,amidosulfuron, amitrole, aminocyclopyrachlor, aminopyralid, amibuzin,amiprophos-methyl, ametridione, ametryn, alachlor, allidochlor,alloxydim, alorac, isouron, isocarbamid, isoxachlortole, isoxapyrifop,isoxaflutole, isoxaben, isocil, isonoruron, isoproturon, isopropalin,isopolinate, isomethiozin, inabenfide, ipazine, ipfencarbazone,iprymidam, imazaquin, imazapic, imazapyr, imazamethapyr, imazamethabenz,imazamethabenz-methyl, imazamox, imazethapyr, imazosulfuron, indaziflam,indanofan, indolebutyric acid, uniconazole-P, eglinazine, esprocarb,ethametsulfuron, ethametsulfuron-methyl, ethalfluralin, ethiolate,ethychlozate-ethyl, ethidimuron, etinofen, ethephon, ethoxysulfuron,ethoxyfen, etnipromid, ethofumesate, etobenzanid, epronaz, erbon,endothal, oxadiazon, oxadiargyl, oxaziclomefone, oxasulfuron,oxapyrazon, oxyfluorfen, oryzalin, orthosulfamuron, orbencarb,

cafenstrole, cambendichlor, carbasulam, carfentrazone,carfentrazone-ethyl, karbutilate, carbetamide, carboxazole, quizalofop,quizalofop-P, quizalofop-ethyl, xylachlor, quinoclamine, quinonamid,quinclorac, quinmerac, cumyluron, cliodinate, glyphosate, glufosinate,glufosinate-P, credazine, clethodim, cloxyfonac, clodinafop,clodinafop-propargyl, chlorotoluron, clopyralid, cloproxydim, cloprop,chlorbromuron, clofop, clomazone, chlomethoxynil, chlomethoxyfen,clomeprop, chlorazifop, chlorazine, cloransulam, chloranocryl,chloramben, cloransulam-methyl, chloridazon, chlorimuron,chlorimuron-ethyl, chlorsulfuron, chlorthal, chlorthiamid, chlortoluron,chlornitrofen, chlorfenac, chlorfenprop, chlorbufam, chlorflurazole,chlorflurenol, chlorprocarb, chlorpropham, chlormequat, chloreturon,chloroxynil, chloroxuron, chloropon,saflufenacil, cyanazine, cyanatryn, di-allate, diuron, diethamquat,dicamba, cycluron, cycloate, cycloxydim, diclosulam, cyclosulfamuron,dichlorprop, dichlorprop-P, dichlobenil, diclofop, diclofop-methyl,dichlormate, dichloralurea, diquat, cisanilide, disul, siduron,dithiopyr, dinitramine, cinidon-ethyl, dinosam, cinosulfuron, dinoseb,dinoterb, dinofenate, dinoprop, cyhalofop-butyl, diphenamid,difenoxuron, difenopenten, difenzoquat, cybutryne, cyprazine, cyprazole,diflufenican, diflufenzopyr, dipropetryn, cypromid, cyperquat,gibberellin, simazine, dimexano, dimethachlor, dimidazon, dimethametryn,dimethenamid, simetryn, simeton, dimepiperate, dimefuron, cinmethylin,swep, sulglycapin, sulcotrione, sulfallate, sulfentrazone,sulfosulfuron, sulfometuron, sulfometuron-methyl, secbumeton,sethoxydim, sebuthylazine,terbacil, daimuron, dazomet, dalapon, thiazafluron, thiazopyr,thiencarbazone, thiencarbazone-methyl, tiocarbazil, tioclorim,thiobencarb, thidiazimin, thidiazuron, thifensulfuron,thifensulfuron-methyl, desmedipham, desmetryn, tetrafluron, thenylchlor,tebutam, tebuthiuron, terbumeton, tepraloxydim, tefuryltrione,tembotrione, delachlor, terbacil, terbucarb, terbuchlor, terbuthylazine,terbutryn, topramezone, tralkoxydim, triaziflam, triasulfuron,tri-allate, trietazine, tricamba, triclopyr, tridiphane, tritac,tritosulfuron, triflusulfuron, triflusulfuron-methyl, trifluralin,trifloxysulfuron, tripropindan, tribenuron-methyl, tribenuron, trifop,trifopsime, trimeturon, naptalam, naproanilide, napropamide,nicosulfuron, nitralin, nitrofen, nitrofluorfen, nipyraclofen, neburon,norflurazon, noruron,barban, paclobutrazol, paraquat, parafluron, haloxydine, haloxyfop,haloxyfop-P, haloxyfop-methyl, halosafen, halosulfuron,halosulfuron-methyl, picloram, picolinafen, bicyclopyrone, bispyribac,bispyribac-sodium, pydanon, pinoxaden, bifenox, piperophos, hymexazol,pyraclonil, pyrasulfotole, pyrazoxyfen, pyrazosulfuron,pyrazosulfuron-ethyl, pyrazolate, bilanafos, pyraflufen-ethyl, pyriclor,pyridafol, pyrithiobac, pyrithiobac-sodium, pyridate, pyriftalid,pyributicarb, pyribenzoxim, pyrimisulfan, primisulfuron,pyriminobac-methyl, pyroxasulfone, pyroxsulam,fenasulam, phenisopham, fenuron, fenoxasulfone, fenoxaprop,fenoxaprop-P, fenoxaprop-ethyl, phenothiol, fenoprop, phenobenzuron,fenthiaprop, fenteracol, fentrazamide, phenmedipham, phenmedipham-ethyl,butachlor, butafenacil, butamifos, buthiuron, buthidazole, butylate,buturon, butenachlor, butroxydim, butralin, flazasulfuron, flamprop,furyloxyfen, prynachlor, primisulfuron-methyl, fluazifop, fluazifop-P,fluazifop-butyl, fluazolate, fluroxypyr, fluothiuron, fluometuron,fluoroglycofen, flurochloridone, fluorodifen, fluoronitrofen,fluoromidine, flucarbazone, flucarbazone-sodium, fluchloralin,flucetosulfuron, fluthiacet, fluthiacet-methyl, flupyrsulfuron,flufenacet, flufenican, flufenpyr, flupropacil, flupropanate, flupoxam,flumioxazin, flumiclorac, flumiclorac-pentyl, flumipropyn, flumezin,fluometuron, flumetsulam, fluridone, flurtamone, fluroxypyr,pretilachlor, proxan, proglinazine, procyazine, prodiamine, prosulfalin,prosulfuron, prosulfocarb, propaquizafop, propachlor, propazine,propanil, propyzamide, propisochlor, prohydrojasmon, propyrisulfuron,propham, profluazol, profluralin, prohexadione-calcium,propoxycarbazone, propoxycarbazone-sodium, profoxydim, bromacil,brompyrazon, prometryn, prometon, bromoxynil, bromofenoxim, bromobutide,bromobonil, florasulam,hexachloroacetone, hexazinone, pethoxamid, benazolin, penoxsulam,pebulate, beflubutamid, vernolate, perfluidone, bencarbazone, benzadox,benzipram, benzylaminopurine, benzthiazuron, benzfendizone, bensulide,bensulfuron-methyl, benzoylprop, benzobicyclon, benzofenap, benzofluor,bentazone, pentanochlor, benthiocarb, pendimethalin, pentoxazone,benfluralin, benfuresate, fosamine, fomesafen, foramsulfuron,forchlorfenuron, maleic hydrazide, mecoprop, mecoprop-P, medinoterb,mesosulfuron, mesosulfuron-methyl, mesotrione, mesoprazine,methoprotryne, metazachlor, methazole, metazosulfuron,methabenzthiazuron, metamitron, metamifop, metam, methalpropalin,methiuron, methiozolin, methiobencarb, methyldymron, metoxuron,metosulam, metsulfuron, metsulfuron-methyl, metflurazon, metobromuron,metobenzuron, methometon, metolachlor, metribuzin, mepiquat-chloride,mefenacet, mefluidide, monalide, monisouron, monuron, monochloroaceticacid, monolinuron, molinate, morfamquat, iodosulfuron,iodosulfuron-methyl-sodium, iodobonil, iodomethane, lactofen, linuron,rimsulfuron, lenacil, rhodethanil, calcium peroxide and methyl bromide.

Exemplary biopesticides used for the same purposes as above includeviral formulations such as nuclear polyhedrosis viruses (NPV),granulosis viruses (GV), cytoplasmic polyhedrosis viruses (CPV) andentomopox viruses (EPV); microbial pesticides used as an insecticide ora nematicide, such as Monacrosporium phymatophagum, Steinernemacarpocapsae, Steinernema kushidai and Pasteuria penetrans; microbialpesticides used as a microbicide, such as Trichoderma lignorum,Agrobacterium radiobactor, avirulent Erwinia carotovora and Bacillussubtilis; and biopesticides used as a herbicide, such as Xanthomonascampestris. Such a combined use of the agricultural and horticulturalinsecticide of the present invention with the foregoing biopesticide asa mixture can be expected to provide the same effect as above.

Other examples of the biopesticides include natural predators such asEncarsia formosa, Aphidius colemani, Aphidoletes aphidimyza, Diglyphusisaea, Dacnusa sibirica, Phytoseiulus persimilis, Amblyseius cucumerisand Orius sauteri; microbial pesticides such as Beauveria brongniartii;and pheromones such as (Z)-10-tetradecenyl acetate,(E,Z)-4,10-tetradecadienyl acetate, (Z)-8-dodecenyl acetate,(Z)-1-tetradecenyl acetate, (Z)-13-icosen-10-one and14-methyl-1-octadecene.

The present invention also includes an animal ectoparasite control agentcomprising the compound of the present invention, an N-oxide thereof ora salt thereof as an active ingredient; and a method for controllinganimal ectoparasites, comprising treating animal ectoparasites with aneffective amount of the animal ectoparasite control agent. The compoundof the present invention can be used by spot-on or pour-on applicationusually to one site or two sites on the skin of an animal such as a cator a dog. The application area is usually 5 to 10 cm². Once applied, thecompound of the present invention preferably diffuses throughout theanimal's body and then dries without crystallization or changes invisual appearance or texture. The preferable amount of the compound usedis selected from the range of 0.1 to 10 mL according to the weight ofthe animal, and in particular, is about 0.5 to 1 mL for a cat and about0.3 to 3 mL for a dog.

The ectoparasite control agent of the present invention is effectiveagainst, for example, the following animal ectoparasites. Siphonapteraparasites include the species of the genus Pulex such as Pulex irritans;the species of the genus Ctenocephalides such as Ctenocephalides felisand Ctenocephalides canis; the species of the genus Xenopsylla such asXenopsylla cheopis; the species of the genus Tunga such as Tungapenetrans; the species of the genus Echidnophaga such as Echidnophagagallinacea; and the species of the genus Nosopsyllus such as Nosopsyllusfasciatus.

Siphunculata parasites include the species of the genus Pediculus suchas Pediculus humanus capitis; the species of the genus Pthirus such asPthirus pubis; the species of the genus Haematopinus such asHaematopinus eurysternus and Haematopinus suis; the species of the genusDamalinia such as Damalinia ovis and Damalinia bovis; the species of thegenus Linognathus such as Linognathus vituli and Linognathus ovillus(parasitic on the trunk of a sheep's body); and the species of the genusSolenopotes such as Solenopotes capillatus.

Mallophaga parasites include the species of the genus Menopon such asMenopon gallinae; Trimenopon spp.; Trinoton spp.; the species of thegenus Trichodectes such as Trichodectes canis; the species of the genusFelicola such as Felicola subrostratus; the species of the genusBovicola such as Bovicola bovis; the species of the genus Menacanthussuch as Menacanthus stramineus; Werneckiella spp.; and Lepikentron spp.

Hemiptera parasites include the species of the genus Cimex such as Cimexlectularius and Cimex hemipterus; the species of the genus Reduvius suchas Reduvius senilis; the species of the genus Arilus such as Ariluscritatus; the species of the genus Rhodnius such as Rhodnius prolixus;the species of the genus Triatoma such as Triatoma rubrofasciata; andPanstrongylus spp.

Acarina parasites include the species of the genus Amblyomma such asAmblyomma americanum and Amblyomma maculatum; the species of the genusBoophilus such as Boophilus microplus and Boophilus annulatus; thespecies of the genus Dermacentor such as Dermacentor variabilis,Dermacentor taiwanicus and Dermacentor andersoni; the species of thegenus Haemaphysalis such as Haemaphysalis longicornis, Haemaphysalisflava and Haemaphysalis campanulata; the species of the genus Ixodessuch as Ixodes ovatus, Ixodes persulcatus, Ixodes scapularis, Ixodespacificus and Ixodes holocyclus; the species of the genus Rhipicephalussuch as Rhipicephalus sanguineus and Rhipicephalus appendiculatus; thespecies of the genus Argas such as Argas persicus; the species of thegenus Ornithodoros such as Ornithodoros hermsi and Ornithodorosturicata; the species of the genus Psoroptes such as Psoroptes ovis andPsoroptes equi; the species of the genus Knemidocoptes such asKnemidocoptes mutans; the species of the genus Notoedres such asNotoedres cati and Notoedres muris; the species of the genus Sarcoptessuch as Sarcoptes scabiei; the species of the genus Otodectes such asOtodectes cynotis; the species of the genus Listrophorus such asListrophorus gibbus; Chorioptes spp.; Hypodectes spp.; Pterolichus spp.;Cytodites spp.; Laminosioptes spp.; the species of the genus Dermanyssussuch as Dermanyssus gallinae; the species of the genus Ornithonyssussuch as Ornithonyssus sylviarum and Ornithonyssus bacoti; the species ofthe genus Varroa such as Varroa jacobsoni; the species of the genusCheyletiella such as Cheyletiella yasguri and Cheyletiella blakei;Ornithocheyletia spp.; the species of the genus Demodex such as Demodexcanis and Demodex cati; Myobia spp.; Psorergates spp.; and the speciesof the genus Trombicula such as Trombicula akamushi, Trombicula pallidaand Trombicula scutellaris. Preferred are Siphonaptera parasites,Siphunculata parasites and Acarina parasites.

The animals to which the ectoparasite control agent of the presentinvention is administrable can be host animals for the above-mentionedanimal ectoparasites. Such animals are usually homeotherms andpoikilotherms which are bred as domestic animals or pets. Suchhomeotherms include mammals such as cattle, buffalos, sheep, goats,pigs, camels, deer, fallow deer, reindeer, horses, donkeys, dogs, cats,rabbits, ferrets, mice, rats, hamsters, squirrels and monkeys;fur-bearing animals such as minks, chinchillas and raccoons; and birdssuch as chickens, geese, turkeys, domestic ducks, pigeons, parrots andquails. The above-mentioned poikilotherms include reptiles such astortoises, sea turtles, pond sliders, Japanese pond turtles, lizards,iguanas, chameleons, geckos, pythons, colubrid snakes and cobras.Preferred are homeotherms, and more preferred are mammals such as dogs,cats, cattle, horses, pigs, sheep and goats.

The compounds of the present invention have excellent biologicalcharacteristics as described above, and in addition, have lowenvironmental burden, as exemplified by being easily degradable in theenvironment and having less impact on useful organisms such ashoneybees.

Hereinafter, the production examples of representative compounds of thepresent invention and their intermediates will be described in moredetail, but the present invention is not limited only to these examples.

EXAMPLES Reference Example 1 Production Method of2-methyl-1-phenylpropan-2-yl3-(3-ethylthio-5-trifluoromethylpyridin-2-yl)-2-(3-nitro-5-trifluoromethylpyridin-2-yl)-3-oxo-propionate

Sodium hydride (240 mg, 3 Eq) was dissolved in dimethylacetamide (DMA)(2 mL). To this, a DMA solution (2 mL) of 2-methyl-1-phenylpropan-2-yl3-(3-ethylthio-5-trifluoromethylpyridin-2-yl)-3-oxo-propionate (895 mg,2 mmol) was slowly added under ice cooling, and the mixture was stirredfor 30 minutes. Then, a DMA solution (2 mL) of2-chloro-3-nitro-5-trifluoromethylpyridine (454 mg, 1 Eq) was slowlyadded, and the mixture was stirred at room temperature for four and halfhours. Water and 3 N hydrochloric acid were added to the reactionmixture, and ethyl acetate extraction was performed. The organic layerwas concentrated, and the residue was subjected to column chromatographyto give the desired compound, i.e., 2-methyl-1-phenylpropan-2-yl3-(3-ethylthio-5-trifluoromethylpyridin-2-yl)-2-(3-nitro-5-trifluoromethylpyridin-2-yl)-3-oxo-propionate(653 mg, containing about 20% nitropyridine (starting material)).

Reference Example 2 Production Method of1-(3-ethylthio-5-trifluoromethylpyridin-2-yl)-2-(3-nitro-5-trifluoromethylpyridin-2-yl)ethanone

2-Methyl-1-phenylpropan-2-yl3-(3-ethylthio-5-trifluoromethylpyridin-2-yl)-2-(3-nitro-5-trifluoromethylpyridin-2-yl)-3-oxo-propionate(653 mg, about 0.4 mmol) was dissolved in trifluoroacetic acid (5 mL),and the solution was heated at 80° C. with stirring for 0.5 hour. Thereaction mixture was concentrated, and the residue was subjected tocolumn chromatography to give the desired compound, i.e.,1-(3-ethylthio-5-trifluoromethylpyridin-2-yl)-2-(3-nitro-5-trifluoromethylpyridin-2-yl)ethanone(172 mg, 98%).

Reference Example 3 Production Method of2-(3-ethylthio-5-trifluoromethylpyridin-2-yl)-6-trifluoromethyl-1H-pyrrolo[3,2-b]pyridine

Acetic acid (5 mL) and iron powder (109 mg, 5 Eq) were added to1-(3-ethylthio-5-trifluoromethylpyridin-2-yl)-2-(3-nitro-5-trifluoromethylpyridin-2-yl)ethanone(171 mg, 0.39 mmol), and the mixture was stirred at 80° C. for 1 hour.After cooling to room temperature, water and ethyl acetate were added,and ethyl acetate extraction was performed 3 times. The organic layerwas concentrated, and the residue was subjected to column chromatographyto give the desired compound, i.e.,2-(3-ethylthio-5-trifluoromethylpyridin-2-yl)-6-trifluoromethyl-1H-pyrrolo[3,2-b]pyridine(98 mg, 65%).

Reference Example 4 Production Method of2-(3-ethylthio-5-trifluoromethylpyridin-2-yl)-1-(tert-butoxycarbonyl)-6-trifluoromethyl-1H-pyrrolo[3,2-b]pyridine

To a tetrahydrofuran (THF) solution (40 mL) of2-(3-ethylthio-5-trifluoromethylpyridin-2-yl)-6-trifluoromethyl-1H-pyrrolo[3,2-b]pyridine(4.0 g), 0.25 g of DMAP (4-dimethylaminopyridine) and Boc₂O (2.6 mL)were added, and the mixture was stirred at room temperature overnight.After the completion of the reaction, a saturated aqueous sodiumhydrogen carbonate solution was added, and ethyl acetate extraction wasperformed. The organic layer was dried over anhydrous magnesium sulfateand then dried in vacuo. The residue was purified by silica gelchromatography to give the desired compound (4.8 g, quantitative).

Reference Example 5 Production Method of2-(3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl)-1-tert-butoxycarbonyl-6-trifluoromethyl-1H-pyrrolo[3,2-b]pyridine

To an ethyl acetate solution (74 mL) of the2-(3-ethylthio-5-trifluoromethylpyridin-2-yl)-1-tert-butoxycarbonyl-6-trifluoromethyl-1H-pyrrolo[3,2-b]pyridine(4.1 g) produced in the previous step, m-chloroperoxybenzoic acid (4.2g) was added at room temperature, and the mixture was stirred for 2hours. After the completion of the reaction, a saturated aqueous sodiumhydrogen carbonate solution and a saturated aqueous sodium thiosulfatesolution were added, and ethyl acetate extraction was performed. Theorganic layer was washed with a saturated aqueous sodium hydrogencarbonate solution, dried over anhydrous magnesium sulfate and thendried in vacuo. The residue was purified by silica gel chromatography togive the desired compound (3.2 g, 72%).

Reference Example 6 Production Method of2-(3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl)-6-trifluoromethyl-1H-pyrrolo[3,2-b]pyridine

To the2-(3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl)-1-tert-butoxycarbonyl-6-trifluoromethyl-1H-pyrrolo[3,2-b]pyridineproduced in the previous step, trifluoroacetic acid (TFA) (10 mL) wasadded, and the mixture was stirred at room temperature overnight. Afterthe completion of the reaction, the reaction mixture was dried in vacuo.The residue was purified by silica gel chromatography to give thedesired compound (0.081 g, 81% (two steps)).

Example 1 Production Method of2-(3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl)-3-chloro-6-trifluoromethyl-1H-pyrrolo[3,2-b]pyridine(Compound Number 1-76)

To an acetonitrile solution (2 mL) of2-(3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl)-6-trifluoromethyl-1H-pyrrolo[3,2-b]pyridine(0.24 g), sulfuryl chloride (0.1 mL) was added at room temperature, andthe mixture was stirred for 5 hours. After the completion of thereaction, a saturated aqueous sodium hydrogen carbonate solution and asaturated aqueous sodium thiosulfate solution were added, the mixturewas stirred for 2 hours, and ethyl acetate extraction was performed. Theorganic layer was dried over anhydrous magnesium sulfate and then driedin vacuo. The residue was purified by silica gel chromatography to givethe desired compound (0.15 g, 71%).

Example 2 Production Method of2-(3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl)-3-bromo-6-trifluoromethyl-1H-pyrrolo[3,2-b]pyridine(Compound Number 1-77)

To an acetonitrile solution (5 mL) of2-(3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl)-6-trifluoromethyl-1H-pyrrolo[3,2-b]pyridine(0.5 g), NBS (0.2 g) was added at room temperature, and the mixture wasstirred for 2 hours. After the completion of the reaction, a saturatedaqueous sodium hydrogen carbonate solution and a saturated aqueoussodium thiosulfate solution were added, and ethyl acetate extraction wasperformed. The organic layer was dried over anhydrous magnesium sulfateand then dried in vacuo. The residue was purified by silica gelchromatography to give the desired compound (0.33 g, 70%).

Example 3 Production Method of2-(3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl)-3-fluoro-6-trifluoromethyl-1H-pyrrolo[3,2-b]pyridine(Compound Number 1-75)

To an acetonitrile solution (1 mL) of2-(3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl)-3-bromo-6-trifluoromethyl-1H-pyrrolo[3,2-b]pyridine(0.056 g), NaHCO₃ (0.02 g) and Selectfluor (0.09 g) were added at roomtemperature, and the mixture was stirred at room temperature overnight.After the completion of the reaction, a saturated aqueous sodiumhydrogen carbonate solution and a saturated aqueous sodium thiosulfatesolution were added, and ethyl acetate extraction was performed. Theorganic layer was dried over anhydrous magnesium sulfate and then driedin vacuo. The residue was purified by silica gel chromatography to givethe desired compound (0.041 g, 83%).

Example 4 Production Method of1-acetyl-2-(3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl)-3-chloro-6-trifluoromethyl-1H-pyrrolo[3,2-b]pyridine(Compound Number 3-3)

To a THF solution (1 mL) of2-(3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl)-3-chloro-6-trifluoromethyl-1H-pyrrolo[3,2-b]pyridine(0.05 g), DMAP (0.010 g) and acetic anhydride (0.020 mL) were added, andthe mixture was stirred at room temperature overnight. After thecompletion of the reaction, the reaction mixture was dried in vacuo. Theresidue was purified by silica gel chromatography to give the desiredcompound (0.29 g, 98%).

Hereinafter, formulation examples are shown, but the present inventionis not limited thereto. In the formulation examples, “part” means partby weight.

Formulation Example 1

Compound of the present invention 10 parts Xylene 70 partsN-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl 10parts ether and calcium alkylbenzene sulfonate

The above ingredients are uniformly mixed for dissolution to give anemulsifiable concentrate formulation.

Formulation Example 2

Compound of the present invention  3 parts Clay powder 82 partsDiatomite powder 15 parts

The above ingredients are uniformly mixed and then pulverized to give adust formulation.

Formulation Example 3

Compound of the present invention 5 parts Mixture of bentonite powderand clay powder 90 parts  Calcium lignosulfonate 5 parts

The above ingredients are uniformly mixed. After addition of anappropriate volume of water, the mixture is kneaded, granulated anddried to give a granular formulation.

Formulation Example 4

Compound of the present invention 20 parts Kaolin and synthetichigh-dispersion 75 parts silicic acid Mixture of polyoxyethylenenonylphenyl  5 parts ether and calcium alkylbenzene sulfonate

The above ingredients are uniformly mixed and then pulverized to give awettable powder formulation.

Hereinafter, test examples in connection with the present invention areshown, but the present invention is not limited thereto.

Test Example 1

Test for Control Efficacy on Myzus persicae

Chinese cabbage plants were planted in plastic pots (diameter: 8 cm,height: 8 cm), Green peach aphids (Myzus persicae) were propagated onthe plants, and the number of surviving Green peach aphids in each potwas counted. The condensed heterocyclic compounds represented by thegeneral formula (1) of the present invention or salts thereof wereseparately dispersed in water and diluted to 500 ppm. The agrochemicaldispersions were applied to the foliage of the potted Chinese cabbageplants. After the plants were air-dried, the pots were kept in agreenhouse. At 6 days after the foliar application, the number ofsurviving Green peach aphids on the Chinese cabbage plant in each potwas counted, the control rate was calculated according to the formulashown below, and the control efficacy was evaluated according to thecriteria shown below.Control rate=100−{(T×Ca)/(Ta×C)}×100  [Math. 1]Ta: the number of survivors before the foliar application in a treatmentplotT: the number of survivors after the foliar application in a treatmentplotCa: the number of survivors before the foliar application in anon-treatment plotC: the number of survivors after the foliar application in anon-treatment plotCriteriaA: the control rate is 100%.B: the control rate is 90 to 99%.C: the control rate is 80 to 89%.D: the control rate is 50 to 79%.

As a result, the compounds 1-3, 1-4, 1-7, 1-8, 1-40, 1-41, 1-44, 1-45,1-46, 1-48, 1-50, 1-75, 1-76, 1-77, 1-78, 1-79, 1-80, 1-81, 1-82, 1-95,1-96, 1-97, 1-98, 1-99, 1-100, 1-101, 1-102, 1-103, 1-104, 1-105, 1-106,1-107, 1-108, 1-109, 1-110, 1-111, 1-112, 1-113, 1-114, 1-115, 1-120,1-121, 1-122, 1-123, 1-124, 1-125, 1-126, 1-127, 1-128, 1-129, 1-130,2-74, 2-93, 3-1, 3-2, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-11,3-12, 3-13, 3-14, 3-15, 3-16, 3-17, 3-20, 3-21, 3-22, 3-24, 3-25, 3-27,3-31, 3-22, 3-37, 3-40, 3-44, 3-45, 3-46, 3-47, 3-48, 3-49, 3-50, 3-51,3-52, 3-53, 3-54, 3-55, 4-1, 5-1, 5-2, 5-3 and 5-4 of the presentinvention showed the activity level evaluated as A.

Test Example 2

Insecticidal Test on Laodelphax striatellus

The condensed heterocyclic compounds represented by the general formula(1) of the present invention or salts thereof were separately dispersedin water and diluted to 500 ppm. Rice plant seedlings (variety:Nihonbare) were dipped in the agrochemical dispersions for 30 seconds.After air-dried, each seedling was put into a separate glass test tubeand inoculated with ten 3rd-instar larvae of Laodelphax striatellus, andthen the glass test tubes were capped with cotton plugs. At 8 days afterthe inoculation, the numbers of surviving larvae and dead larvae werecounted, the corrected mortality rate was calculated according to theformula shown below, and the insecticidal efficacy was evaluatedaccording to the criteria shown below.Corrected mortality rate (%)=100×(Survival rate in a non-treatmentplot−Survival rate in a treatment plot)/Survival rate in a non-treatmentplot  [Math. 2]Corrected Mortality Rate A: the corrected mortality rate is 100%.B: the corrected mortality rate is 90 to 99%.C: the corrected mortality rate is 80 to 89%.D: the corrected mortality rate is 50 to 79%.

As a result, the compounds 1-3, 1-4, 1-7, 1-8, 1-40, 1-41, 1-44, 1-45,1-46, 1-48, 1-50, 1-75, 1-76, 1-77, 1-78, 1-79, 1-80, 1-81, 1-82, 1-95,1-96, 1-97, 1-98, 1-99, 1-100, 1-101, 1-102, 1-103, 1-104, 1-105, 1-106,1-107, 1-108, 1-109, 1-110, 1-111, 1-112, 1-113, 1-114, 1-115, 1-120,1-121, 1-122, 1-123, 1-124, 1-125, 1-126, 1-127, 1-128, 1-129, 1-130,2-74, 2-93, 3-1, 3-2, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-11,3-12, 3-13, 3-14, 3-15, 3-16, 3-17, 3-20, 3-21, 3-22, 3-24, 3-25, 3-27,3-31, 3-22, 3-37, 3-40, 3-44, 3-45, 3-46, 3-47, 3-48, 3-49, 3-50, 3-51,3-52, 3-53, 3-54, 3-55, 4-1, 5-1, 5-2, 5-3 and 5-4 of the presentinvention showed the activity level evaluated as A.

Test Example 3

Insecticidal Test on Plutella xylostella

Adults of Plutella xylostella were released onto Chinese cabbageseedlings and allowed to lay eggs thereon. At 2 days after the releaseof the adults, the Chinese cabbage seedlings with laid eggs were dippedfor about 30 seconds in agrochemical dispersions diluted to 500 ppm,each of which contained a different condensed heterocyclic compoundrepresented by the general formula (1) of the present invention as anactive ingredient. After air-dried, the seedlings were kept in athermostatic chamber at 25° C. At 6 days after the dip treatment, thenumber of hatched larvae per plot was counted, the mortality rate wascalculated according to the formula shown below, and the insecticidalefficacy was evaluated according to the criteria of Test Example 2. Thistest was conducted in triplicate using 10 adults of Plutella xylostellaper plot.Corrected mortality rate (%)=100×(Number of hatched larvae in anon-treatment plot−Number of hatched larvae in a treatment plot)/Numberof hatched larvae in a non-treatment plot  [Math. 3]

As a result, the compounds 1-3, 1-4, 1-7, 1-8, 1-40, 1-41, 1-44, 1-45,1-46, 1-48, 1-50, 1-75, 1-76, 1-77, 1-78, 1-79, 1-80, 1-81, 1-82, 1-95,1-96, 1-97, 1-98, 1-99, 1-100, 1-101, 1-102, 1-103, 1-104, 1-105, 1-106,1-107, 1-108, 1-109, 1-110, 1-111, 1-112, 1-113, 1-114, 1-115, 1-120,1-121, 1-122, 1-123, 1-124, 1-125, 1-126, 1-127, 1-128, 1-129, 1-130,2-74, 2-93, 3-1, 3-2, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-11,3-12, 3-13, 3-14, 3-15, 3-16, 3-17, 3-20, 3-21, 3-22, 3-24, 3-25, 3-27,3-31, 3-22, 3-37, 3-40, 3-44, 3-45, 3-46, 3-47, 3-48, 3-49, 3-50, 3-51,3-52, 3-53, 3-54, 3-55, 4-1, 5-1, 5-2, 5-3 and 5-4 of the presentinvention showed the activity level evaluated as A.

INDUSTRIAL APPLICABILITY

The compounds of the present invention are highly effective for thecontrol of a wide range of agricultural and horticultural pests and thusare useful.

The invention claimed is:
 1. A condensed heterocyclic compoundrepresented by the general formula (1):

wherein: R¹ represents: (a1) a halogen atom; (a2) a cyano group; (a3) a(C₁-C₆) alkyl group; (a4) a (C₃-C₆) cycloalkyl group; (a5) a (C₂-C₆)alkenyl group; (a6) a (C₂-C₆) alkynyl group; (a7) a (C₁-C₆)alkylcarbonyl group; or (a8) a (C₁-C₆) alkoxycarbonyl group, R²represents: (b1) a hydrogen atom; (b2) a (C₁-C₆) alkyl group; (b3) a(C₁-C₆) alkylcarbonyl group; (b4) a (C₁-C₆) alkoxycarbonyl group; (b5) ahalo (C₁-C₆) alkoxy group; (b6) a (C₁-C₆) alkoxy (C₁-C₆) alkyl group;(b7) a (C₁-C₆) alkylthio (C₁-C₆) alkyl group; (b8) a (C₂-C₆) alkenylgroup; (b9) a (C₂-C₆) alkynyl group; or (b10) a (C₃-C₆) cycloalkyl(C₁-C₆) alkyl group, R³ represents: (c1) a hydrogen atom; (c2) a halogenatom; (c3) a cyano group; (c4) a nitro group; (c5) a (C₁-C₆) alkylgroup; (c6) a (C₃-C₆) cycloalkyl group; (c7) a cyano (C₃-C₆) cycloalkylgroup; (c8) a (C₁-C₆) alkoxy group; (c9) a halo (C₁-C₆) alkyl group;(c10) a halo (C₁-C₆) alkoxy group; (c11) a (C₁-C₆) alkylthio group;(c12) a halo (C₁-C₆) alkylthio group; (c13) a (C₁-C₆) alkylsulfinylgroup; (c14) a halo (C₁-C₆) alkylsulfinyl group; (c15) a (C₁-C₆)alkylsulfonyl group; or (c16) a halo (C₁-C₆) alkylsulfonyl group, R⁴ andR⁵ may be the same or different, and each represent: (d1) a hydrogenatom; (d2) a halogen atom; (d3) a cyano group; (d4) a nitro group; (d4)a formyl group; (d5) a (C₁-C₆) alkyl group; (d6) a (C₁-C₆) alkoxy group;(d7) a (C₃-C₆) cycloalkyl group; (d8) an R⁶(R⁷)N group, wherein R⁶ andR⁷ may be the same or different, and each represent a hydrogen atom, a(C₁-C₆) alkyl group, a (C₃-C₆) cycloalkyl group, a (C₃-C₆) cycloalkyl(C₁-C₆) alkyl group, a halo (C₁-C₆) alkyl group, a (C₁-C₆) alkylcarbonylgroup, a (C₁-C₆) alkoxycarbonyl group, a phenyl group or a phenyl(C₁-C₆) alkyl group; (d9) a C(R⁶)═NOR′ group, wherein R⁶ and R⁷ are asdefined above; (d10) a halo (C₁-C₆) alkyl group; (d11) a halo (C₁-C₆)alkoxy group; (d12) a (C₁-C₆) alkylthio group; (d13) a halo (C₁-C₆)alkylthio group; (d14) a (C₁-C₆) alkylsulfinyl group; (d15) a halo(C₁-C₆) alkylsulfinyl group; (d16) a (C₁-C₆) alkylsulfonyl group; (d17)a halo (C₁-C₆) alkylsulfonyl group; (d18) a (C₁-C₆) alkylcarbonyl group;(d19) an aryl group; (d20) an aryl group having, on the ring, 1 to 5substituting groups, which may be the same or different and are selectedfrom (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) aformyl group, (e) a (C₁-C₆) alkyl group, (f) a halo (C₁-C₆) alkyl group,(g) a (C₁-C₆) alkoxy group, (h) a halo (C₁-C₆) alkoxy group, (i) a(C₃-C₆) cycloalkyl (C₁-C₆) alkoxy group, (j) a (C₁-C₆) alkylthio group,(k) a halo (C₁-C₆) alkylthio group, (l) a (C₁-C₆) alkylsulfinyl group,(m) a halo (C₁-C₆) alkylsulfinyl group, (n) a (C₁-C₆) alkylsulfonylgroup, (o) a halo (C₁-C₆) alkylsulfonyl group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group or (r) a (C₁-C₆)alkoxycarbonyl group; (d21) a heterocyclic group; (d22) a heterocyclicgroup having, on the ring, 1 or 2 substituting groups, which may be thesame or different and are selected from (a) a halogen atom, (b) a cyanogroup, (c) a nitro group, (d) a formyl group, (e) a (C₁-C₆) alkyl group,(f) a halo (C₁-C₆) alkyl group, (g) a (C₁-C₆) alkoxy group, (h) a halo(C₁-C₆) alkoxy group, (i) a (C₃-C₆) cycloalkyl (C₁-C₆) alkoxy group, (j)a (C₁-C₆) alkylthio group, (k) a halo (C₁-C₆) alkylthio group, (l) a(C₁-C₆) alkylsulfinyl group, (m) a halo (C₁-C₆) alkylsulfinyl group, (n)a (C₁-C₆) alkylsulfonyl group, (o) a halo (C₁-C₆) alkylsulfonyl group,(p) a (C₁-C₆) alkylcarbonyl group, (q) a carboxyl group or (r) a (C₁-C₆)alkoxycarbonyl group; (d23) an aryloxy group; (d24) an aryloxy grouphaving, on the ring, 1 to 5 substituting groups, which may be the sameor different and are selected from (a) a halogen atom, (b) a cyanogroup, (c) a nitro group, (d) a formyl group, (e) a (C₁-C₆) alkyl group,(f) a halo (C₁-C₆) alkyl group, (g) a (C₁-C₆) alkoxy group, (h) a halo(C₁-C₆) alkoxy group, (i) a (C₃-C₆) cycloalkyl (C₁-C₆) alkoxy group, (j)a (C₁-C₆) alkylthio group, (k) a halo (C₁-C₆) alkylthio group, (l) a(C₁-C₆) alkylsulfinyl group, (m) a halo (C₁-C₆) alkylsulfinyl group, (n)a (C₁-C₆) alkylsulfonyl group, (o) a halo (C₁-C₆) alkylsulfonyl group,(p) a (C₁-C₆) alkylcarbonyl group, (q) a carboxyl group or (r) a (C₁-C₆)alkoxycarbonyl group; (d25) an aryl (C₁-C₆) alkoxy group; or (d26) anaryl (C₁-C₆) alkoxy group having, on the ring, 1 to 5 substitutinggroups, which may be the same or different and are selected from (a) ahalogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group,(e) a (C₁-C₆) alkyl group, (f) a halo (C₁-C₆) alkyl group, (g) a (C₁-C₆)alkoxy group, (h) a halo (C₁-C₆) alkoxy group, (i) a (C₃-C₆) cycloalkyl(C₁-C₆) alkoxy group, (j) a (C₁-C₆) alkylthio group, (k) a halo (C₁-C₆)alkylthio group, (l) a (C₁-C₆) alkylsulfinyl group, (m) a halo (C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆) alkylsulfonyl group, (o) a halo(C₁-C₆) alkylsulfonyl group, (p) a (C₁-C₆) alkylcarbonyl group, (q) acarboxyl group or (r) a (C₁-C₆) alkoxycarbonyl group, A and A¹ may bethe same or different, and each represent a nitrogen atom, an N-oxide ora C—R⁸ group, wherein R⁸ represents (e1) a hydrogen atom; (e2) a halogenatom; (e3) a cyano group; (e4) a nitro group; (e5) a formyl group; (e6)a (C₁-C₆) alkyl group; or (e7) a (C₁-C₆) alkoxy group), and m represents0, 1 or 2, an N-oxide thereof or a salt thereof.
 2. The condensedheterocyclic compound, the N-oxide or the salt according to claim 1,wherein: R¹ represents: (a1) a halogen atom; (a2) a cyano group; (a3) a(C₁-C₆) alkyl group; (a5) a (C₂-C₆) alkenyl group; or (a8) a (C₁-C₆)alkoxycarbonyl group, R² represents: (b1) a hydrogen atom; (b2) a(C₁-C₆) alkyl group; (b3) a (C₁-C₆) alkylcarbonyl group; (b4) a (C₁-C₆)alkoxycarbonyl group; (b5) a halo (C₁-C₆) alkoxy group; (b6) a (C₁-C₆)alkoxy (C₁-C₆) alkyl group; (b7) a (C₁-C₆) alkylthio (C₁-C₆) alkylgroup; (b8) a (C₂-C₆) alkenyl group; (b9) a (C₂-C₆) alkynyl group; or(b10) a (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group, R³ represents (c9) ahalo (C₁-C₆) alkyl group, R⁴ and R⁵ may be the same or different, andeach represent: (d2) a halogen atom; (d4) a formyl group; (d6) a (C₁-C₆)alkoxy group; (d7) a (C₃-C₆) cycloalkyl group; (d8) an R⁶(R⁷)N group,wherein R⁶ and R⁷ may be the same or different, and each represent ahydrogen atom, a (C₁-C₆) alkyl group, a (C₃-C₆) cycloalkyl group, a(C₃-C₆) cycloalkyl (C₁-C₆) alkyl group, a halo (C₁-C₆) alkyl group, a(C₁-C₆) alkylcarbonyl group, a (C₁-C₆) alkoxycarbonyl group, a phenylgroup or a phenyl (C₁-C₆) alkyl group; (d9) a C(R⁶)═NOR′ group, whereinR⁶ and R⁷ are as defined above; (d10) a halo (C₁-C₆) alkyl group; (d11)a halo (C₁-C₆) alkoxy group; (d12) a (C₁-C₆) alkylthio group; (d13) ahalo (C₁-C₆) alkylthio group; (d16) a (C₁-C₆) alkylsulfonyl group; (d18)a (C₁-C₆) alkylcarbonyl group; (d20) an aryl group having, on the ring,1 to 5 substituting groups, which may be the same or different and areselected from (a) a halogen atom, (b) a cyano group, (c) a nitro group,(d) a formyl group, (e) a (C₁-C₆) alkyl group, (f) a halo (C₁-C₆) alkylgroup, (g) a (C₁-C₆) alkoxy group, (h) a halo (C₁-C₆) alkoxy group, (i)a (C₃-C₆) cycloalkyl (C₁-C₆) alkoxy group, (j) a (C₁-C₆) alkylthiogroup, (k) a halo (C₁-C₆) alkylthio group, (l) a (C₁-C₆) alkylsulfinylgroup, (m) a halo (C₁-C₆) alkylsulfinyl group, (n) a (C₁-C₆)alkylsulfonyl group, (o) a halo (C₁-C₆) alkylsulfonyl group, (p) a(C₁-C₆) alkylcarbonyl group, (q) a carboxyl group or (r) a (C₁-C₆)alkoxycarbonyl group; (d21) a heterocyclic group; (d22) a heterocyclicgroup having, on the ring, 1 or 2 substituting groups, which may be thesame or different and are selected from (a) a halogen atom, (b) a cyanogroup, (c) a nitro group, (d) a formyl group, (e) a (C₁-C₆) alkyl group,(f) a halo (C₁-C₆) alkyl group, (g) a (C₁-C₆) alkoxy group, (h) a halo(C₁-C₆) alkoxy group, (i) a (C₃-C₆) cycloalkyl (C₁-C₆) alkoxy group, (j)a (C₁-C₆) alkylthio group, (k) a halo (C₁-C₆) alkylthio group, (l) a(C₁-C₆) alkylsulfinyl group, (m) a halo (C₁-C₆) alkylsulfinyl group, (n)a (C₁-C₆) alkylsulfonyl group, (o) a halo (C₁-C₆) alkylsulfonyl group,(p) a (C₁-C₆) alkylcarbonyl group, (q) a carboxyl group or (r) a (C₁-C₆)alkoxycarbonyl group; (d24) an aryloxy group having, on the ring, 1 to 5substituting groups, which may be the same or different and are selectedfrom (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) aformyl group, (e) a (C₁-C₆) alkyl group, (f) a halo (C₁-C₆) alkyl group,(g) a (C₁-C₆) alkoxy group, (h) a halo (C₁-C₆) alkoxy group, (i) a(C₃-C₆) cycloalkyl (C₁-C₆) alkoxy group, (j) a (C₁-C₆) alkylthio group,(k) a halo (C₁-C₆) alkylthio group, (l) a (C₁-C₆) alkylsulfinyl group,(m) a halo (C₁-C₆) alkylsulfinyl group, (n) a (C₁-C₆) alkylsulfonylgroup, (o) a halo (C₁-C₆) alkylsulfonyl group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group or (r) a (C₁-C₆)alkoxycarbonyl group; (d25) an aryl (C₁-C₆) alkoxy group; or (d26) anaryl (C₁-C₆) alkoxy group having, on the ring, 1 to 5 substitutinggroups, which may be the same or different and are selected from (a) ahalogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group,(e) a (C₁-C₆) alkyl group, (f) a halo (C₁-C₆) alkyl group, (g) a (C₁-C₆)alkoxy group, (h) a halo (C₁-C₆) alkoxy group, (i) a (C₃-C₆) cycloalkyl(C₁-C₆) alkoxy group, (j) a (C₁-C₆) alkylthio group, (k) a halo (C₁-C₆)alkylthio group, (l) a (C₁-C₆) alkylsulfinyl group, (m) a halo (C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆) alkylsulfonyl group, (o) a halo(C₁-C₆) alkylsulfonyl group, (p) a (C₁-C₆) alkylcarbonyl group, (q) acarboxyl group or (r) a (C₁-C₆) alkoxycarbonyl group.
 3. The condensedheterocyclic compound, the N-oxide or the salt according to claim 1,wherein: R¹ represents: (a1) a halogen atom; (a2) a cyano group; (a3) a(C₁-C₆) alkyl group; (a5) a (C₂-C₆) alkenyl group; or (a8) a (C₁-C₆)alkoxycarbonyl group, R² represents: (b1) a hydrogen atom; (b2) a(C₁-C₆) alkyl group; (b3) a (C₁-C₆) alkylcarbonyl group; (b4) a (C₁-C₆)alkoxycarbonyl group; (b5) a halo (C₁-C₆) alkoxy group; (b6) a (C₁-C₆)alkoxy (C₁-C₆) alkyl group; (b7) a (C₁-C₆) alkylthio (C₁-C₆) alkylgroup; (b8) a (C₂-C₆) alkenyl group; (b9) a (C₂-C₆) alkynyl group; or(b10) a (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group, R³ represents (c9) ahalo (C₁-C₆) alkyl group, R⁴ and R⁵ may be the same or different, andeach represent: (d2) a halogen atom; (d4) a formyl group; (d6) a (C₁-C₆)alkoxy group; (d7) a (C₃-C₆) cycloalkyl group; (d9) a C(R⁶)═NOR′ group,wherein R⁶ and R⁷ may be the same or different, and each represent ahydrogen atom, a (C₁-C₆) alkyl group, a (C₃-C₆) cycloalkyl group, a(C₃-C₆) cycloalkyl (C₁-C₆) alkyl group, a halo (C₁-C₆) alkyl group, a(C₁-C₆) alkylcarbonyl group, a (C₁-C₆) alkoxycarbonyl group, a phenylgroup or a phenyl (C₁-C₆) alkyl group); (d10) a halo (C₁-C₆) alkylgroup; (d11) a halo (C₁-C₆) alkoxy group; (d20) an aryl group having, onthe ring, 1 to 5 substituting groups, which may be the same or differentand are selected from (a) a halogen atom, (b) a cyano group, (c) a nitrogroup, (d) a formyl group, (e) a (C₁-C₆) alkyl group, (f) a halo (C₁-C₆)alkyl group, (g) a (C₁-C₆) alkoxy group, (h) a halo (C₁-C₆) alkoxygroup, (i) a (C₃-C₆) cycloalkyl (C₁-C₆) alkoxy group, (j) a (C₁-C₆)alkylthio group, (k) a halo (C₁-C₆) alkylthio group, (l) a (C₁-C₆)alkylsulfinyl group, (m) a halo (C₁-C₆) alkylsulfinyl group, (n) a(C₁-C₆) alkylsulfonyl group, (o) a halo (C₁-C₆) alkylsulfonyl group, (p)a (C₁-C₆) alkylcarbonyl group, (q) a carboxyl group or (r) a (C₁-C₆)alkoxycarbonyl group; (d21) a heterocyclic group; (d22) a heterocyclicgroup having, on the ring, 1 or 2 substituting groups, which may be thesame or different and are selected from (a) a halogen atom, (b) a cyanogroup, (c) a nitro group, (d) a formyl group, (e) a (C₁-C₆) alkyl group,(f) a halo (C₁-C₆) alkyl group, (g) a (C₁-C₆) alkoxy group, (h) a halo(C₁-C₆) alkoxy group, (i) a (C₃-C₆) cycloalkyl (C₁-C₆) alkoxy group, (j)a (C₁-C₆) alkylthio group, (k) a halo (C₁-C₆) alkylthio group, (l) a(C₁-C₆) alkylsulfinyl group, (m) a halo (C₁-C₆) alkylsulfinyl group, (n)a (C₁-C₆) alkylsulfonyl group, (o) a halo (C₁-C₆) alkylsulfonyl group,(p) a (C₁-C₆) alkylcarbonyl group, (q) a carboxyl group or (r) a (C₁-C₆)alkoxycarbonyl group; (d24) an aryloxy group having, on the ring, 1 to 5substituting groups, which may be the same or different and are selectedfrom (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) aformyl group, (e) a (C₁-C₆) alkyl group, (f) a halo (C₁-C₆) alkyl group,(g) a (C₁-C₆) alkoxy group, (h) a halo (C₁-C₆) alkoxy group, (i) a(C₃-C₆) cycloalkyl (C₁-C₆) alkoxy group, (j) a (C₁-C₆) alkylthio group,(k) a halo (C₁-C₆) alkylthio group, (l) a (C₁-C₆) alkylsulfinyl group,(m) a halo (C₁-C₆) alkylsulfinyl group, (n) a (C₁-C₆) alkylsulfonylgroup, (o) a halo (C₁-C₆) alkylsulfonyl group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group or (r) a (C₁-C₆)alkoxycarbonyl group; (d25) an aryl (C₁-C₆) alkoxy group; or (d26) anaryl (C₁-C₆) alkoxy group having, on the ring, 1 to 5 substitutinggroups, which may be the same or different and are selected from (a) ahalogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group,(e) a (C₁-C₆) alkyl group, (f) a halo (C₁-C₆) alkyl group, (g) a (C₁-C₆)alkoxy group, (h) a halo (C₁-C₆) alkoxy group, (i) a (C₃-C₆) cycloalkyl(C₁-C₆) alkoxy group, (j) a (C₁-C₆) alkylthio group, (k) a halo (C₁-C₆)alkylthio group, (l) a (C₁-C₆) alkylsulfinyl group, (m) a halo (C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆) alkylsulfonyl group, (o) a halo(C₁-C₆) alkylsulfonyl group, (p) a (C₁-C₆) alkylcarbonyl group, (q) acarboxyl group or (r) a (C₁-C₆) alkoxycarbonyl group.
 4. A method ofmaking an agricultural and horticultural insecticide comprisingincorporating the condensed heterocyclic compound, the N-oxide or thesalt thereof according to claim 1 into a solid or liquid formulation. 5.A method for controlling agricultural or horticultural pests, comprisingapplying an effective amount of a composition comprising the condensedheterocyclic compound, the N-oxide or the salt thereof as specified inclaim 1 to plants or soil.
 6. An animal ectoparasite control agentcomprising the condensed heterocyclic compound, the N-oxide or the saltthereof according to claim 1 as an active ingredient.
 7. A method forcontrolling animal ectoparasites, comprising contacting animalectoparasites with an effective amount of the animal ectoparasitecontrol agent according to claim 6.